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15 celebrity couples who ruled the 1990s

14 February 2025 at 08:37
pamela anderson tommy lee 2007
Pamela Anderson and Tommy Lee had a public romance in the 1990s.

Denise Truscello/WireImage/Getty Images

In honor of Valentine's Day, we looked back at the most iconic celebrity couples who ruled the 1990s.

From David and Victoria Beckham to David Bowie and supermodel Iman, some celebrity love stories stood the test of time. Others, like Nicole Kidman and Tom Cruise, ended in scandal or heartbreak. But all left an indelible mark on pop culture.

Here are the most iconic power couples from the '90s.

Bruce Willis and Demi Moore were married throughout the '90s, and they remained on good terms after their split.
Bruce Willis and Demi Moore
Bruce Willis and Demi Moore in 1990.

Ron Galella, Ltd./Ron Galella Collection/Getty Images

Bruce Willis and Demi Moore were married from 1987 until 2000. They met at a movie screening and were married just a few months later in Las Vegas.

"We were moving to the gambling tables when Bruce said, 'I think we should get married.' We'd been joking about it on the flight there, but suddenly it didn't seem like he was kidding," Moore wrote in her memoir, The Sun reported.

Willis and Moore called it quits in 1998 but are still friends. They share three daughters: Rumer, 36; Scout, 33; and Tallulah, 31.

On March 30, 2022, Moore and Willis' family announced that he was stepping back from acting after receiving an aphasia diagnosis.

"We wanted to share that our beloved Bruce has been experiencing some health issues and has recently been diagnosed with aphasia, which is impacting his cognitive abilities," Rumer Willis, his eldest daughter with Demi Moore, said in a post on her account. "As a result of this and with much consideration Bruce is stepping away from the career that has meant so much to him."

"As Bruce always says, 'Live it up' and together we plan to do just that," the statement concluded.

Gwyneth Paltrow and Brad Pitt looked and dressed eerily similar while they were dating.
gwyneth paltrow brad pitt
Gwyneth Paltrow and Brad Pitt in 1996.

Ron Galella, Ltd./Ron Galella Collection/Getty Images

Gwyneth Paltrow and Brad Pitt dated from around 1994 to 1997 after meeting on the set of "Se7en." They were a red-carpet power couple, and they even sported matching haircuts and outfits.

However, despite Pitt proposing, the two ended things in 1997.

"I was such a kid," Paltrow told Howard Stern in 2015, adding, "You can't make that decision when you're 22 years old.

"I wasn't ready, and he was too good for me," she added.

Ben Affleck and Gwyneth Paltrow were also a power couple in the late '90s.
ben affleck gwyneth paltrow
Ben Affleck and Gwyneth Paltrow in 1998.

Ke.Mazur/WireImage/Getty Images

The pair previously met at a dinner party hosted by now-disgraced producer Harvey Weinstein and went on to be costars on the set of "Shakespeare in Love" and "Bounce."

They called things off in 2000.

"I just think we have a very different sort of value system," Gwyneth told Entertainment Weekly in 2003, adding that he was "a great guy."

Paltrow recently gave her blessing to her ex and Jennifer Lopez, who married in July 2022 after initially splitting in 2004. 

When asked about how she felt about Affleck and Lopez finally tying the knot, Paltrow responded, "Love!!! So romantic!!! Very happy for them," in an Instagram Story during a fan Q&A, according to People.

But Lopez and Affleck split again, finalizing their divorce in January 2025.

Winona Ryder and Matt Damon were introduced by Paltrow while she was dating Affleck.
matt damon winona ryder
Winona Ryder and Matt Damon in 2000.

Steve Granitz/WireImage/Getty Images

Winona Ryder and Matt Damon had a brief but public romance, and they even attended the Golden Globes together in 2000. However, not long after that, they split up amicably. 

"Matt couldn't be a greater, nicer guy. I'm really lucky that I'm on good terms with him," Ryder told Black Book in 2009.

Johnny Depp and Winona Ryder got engaged in 1990 but split three years later.
johnny depp winona ryder
Johnny Depp and Winona Ryder in 1990.

Barry King/WireImage/Getty Images

Johnny Depp and Winona Ryder's whirlwind romance became one of the most iconic relationships of the 1990s.

The pair met in 1989 when Ryder was just 18 and Depp was 27, while Ryder was buying a Coke at the premiere of "Great Balls of Fire!" in the lobby of New York's Ziegfeld Theater.

"It was a classic glance," Depp said, according to Rolling Stone, "like the zoom lenses in 'West Side Story,' and everything else gets foggy."

Ryder recalled that when she met Depp, she was a "pure virgin" and had never been in a relationship before.

"There's been nothing in my 27 years that's comparable to the feeling I have with Winona," Depp told People after meeting Ryder.

Five months after meeting, the pair were engaged. Depp also famously got "Winona Forever" tattooed on his right arm, which he altered to "Wino Forever" after the pair split in 1993. 

Kate Moss and Johnny Depp's passionate romance was the talk of the town in the late '90s.
kate moss johnny depp
Kate Moss and Johnny Depp in 1995.

Kevin Mazur Archive/WireImage/Getty Images

Kate Moss and Johnny Depp dated from 1994 to 1998. However, despite only dating a few years, they certainly made an impact as one of the chicest couples of the '90s.

During that time, they had a few famous bust-ups, including, as reported by The New York Times, when Depp destroyed his room at the Mark Hotel in New York City in 1994. Felony mischief charges were dropped after he paid more than $9,000 in fines. Depp also reportedly filled a bathtub with bottles of champagne worth $1,000. 

"There's nobody that's ever really been able to take care of me. Johnny did for a bit. I believed what he said. Like if I said, 'What do I do?' he'd tell me. And that's what I missed when I left," Moss told Vanity Fair in 2012. "I really lost that gauge of somebody I could trust. Nightmare. Years and years of crying. Oh, the tears!"

However, Moss and Depp appear to have reconciled their relationship in recent years. During Depp's tumultuous defamation trial against Amber Heard in 2022, Moss took to the stand to vouch for Depp's character and dispute claims that he once pushed her down the stairs.

Richard Gere and Cindy Crawford married in 1991. At the time, she was 25 and Gere was 42.
richard gere cindy crawford
Richard Gere and Cindy Crawford in 1994.

Dave Benett/Getty Images

The "Pretty Woman" heartthrob and supermodel met at a barbecue hosted by photographer Herb Ritts in the late 1980s. A few years later, the pair spontaneously wed in a Las Vegas ceremony complete with aluminum-foil wedding rings.

However, Gere and Crawford split in 1995 after four years of marriage. 

"I think part of the problem in our relationship was that we were a lot of other things but I don't know if we were ever friends — like peers, because I was young, and he was Richard Gere," she said in an interview with Marc Maron on his podcast in 2016. "And then, as I started kind of growing up and growing into myself — it's hard to change the nature of a relationship once you're already in it."

Crawford also said she and Gere haven't really kept in touch after they went on to marry other people. 

Pamela Anderson and Tommy Lee had a public romance in the 1990s and reconnected time and time again over the years.
pamela anderson tommy lee
Pamela Anderson and Tommy Lee in 1999.

LUCY NICHOLSON/AFP/Getty Images

Pamela Anderson and Tommy Lee got married in 1995, just four days after meeting.

Throughout their four-year marriage, the pair were consistently involved in one scandal or another, from over-the-top public displays of affection to a leaked sex tape that was documented in the 2022 Hulu series "Pam & Tommy."

Anderson and Lee finally called it quits in 1998, but they went on to have an off-and-on relationship over the following decade. They share two children: Brandon Thomas Lee, 28, and Dylan Jagger Lee, 27. 

"I've spoken to Tommy a few times. It's always cordial and we ramble to each other sometimes and I can tell we miss each other's voice. But he's moved on. He has a wife," Anderson said about her relationship with Lee in an interview with Interview Magazine in 2023.

"And the last thing I want to do is be disruptive in anyone's life. Not that I could be. They're probably like, 'Oh god, here she goes again.' But it's part of my story," she continued.

In "Pamela, a Love Story," Anderson's Netflix documentary about her life and relationship with Lee, she spoke to her eldest son, Brandon, about his father, saying she loved him for "all the right reasons."

"I don't think I've ever loved anybody else," she said.

"It's impossible to be with anybody else. But I don't think I can be with Tommy either. It's almost like a punishment," she continued.

Whitney Houston and Bobby Brown had a volatile relationship after meeting in 1989.
Whitney Houston and Bobby Brown
Whitney Houston and Bobby Brown in 1992.

L. Cohen/WireImage/Getty Images

Whitney Houston and Bobby Brown met at the Soul Train Music Awards in 1989, when both were at the top of the music charts. However, it wasn't exactly love at first sight. 

"I and some friends of mine were sitting behind him," Houston told Rolling Stone of their first encounter. "I was hugging them, we were laughing, and I kept hitting Bobby in the back of the head … I leaned over and said, 'Bobby, I'm so sorry.' And he turned around and looked at me like, 'Yeah, well just don't let it happen again.' And I was like, 'Oooooh, this guy doesn't like me.' Well, I always get curious when somebody doesn't like me."

Their relationship weathered many ups and downs. According to Biography, Houston turned down Brown's first marriage proposal, but they were eventually married on July 18, 1992. In March 1993, Bobbi Kristina Brown, their only child, was born.

However, in the mid-2000s, news broke of problems in their marriage, including drug use and rumors of infidelity. During the marriage, Brown had multiple run-ins with the law. CNN reported in 2003 he was accused of striking Houston across the face, however, he was not convicted and denied ever hitting her. Houston also entered rehab on two occasions for her drug abuse.

"I never cheated, I never did none of that stuff," she told Oprah Winfrey in 2009, two years after the pair divorced. "I just did the drugs."

Whitney Houston died on February 11, 2012, after accidentally drowning in her bathtub. Their daughter, Bobbi Kristina, died in 2015.

Hugh Grant and Elizabeth Hurley were together for 13 years before splitting in 2000.
hugh grant elizabeth hurley
Hugh Grant and Elizabeth Hurley in 1999.

Steve Eichner/Getty Images

According to InStyle, Hugh Grant and Liz Hurley met on the set of Spanish film "Remando al viento," or "Rowing With the Wind," in 1987. The pair quickly became one of the most photographed couples in the world.

However, their relationship hit a snag when Grant was famously arrested in 1995 for soliciting lewd conduct with a sex worker named Divine Brown. He was later sentenced to pay a $1,000 fine and attend an AIDS training program, The Guardian reported.

"I felt like I'd been shot," Hurley told Barbara Walters in 1995 of her initial reaction to Grant's indiscretion.

The pair worked through the scandal and stayed together for another five years before breaking up. They've remained friends over the years.

Nicole Kidman and Tom Cruise were together throughout the decade.
Nicole Kidman and Tom Cruise
Nicole Kidman and Tom Cruise in 1990.

Terry McGinnis/WireImage/Getty Images

Nicole Kidman and Tom Cruise met while working on "Days of Thunder" and were married from 1990 to 2001.

"He basically swept me off my feet," Kidman told Vanity Fair in 2002. "I fell madly, passionately in love. And as happens when you fall in love, my whole plan in terms of what I wanted for my life—I was like, 'Forget it. This is it.' I was consumed by it, willingly."

Despite appearing to be one of the most steadfast couples in Hollywood, Kidman and Cruise later divorced.

Cruise went on to marry actress Katie Holmes in 2006, but they divorced in 2012. Also in 2006, Kidman wed country singer Keith Urban, with whom she has two children.

Kurt Cobain and Courtney Love defined the grunge scene of the '90s.
frances bean cobain
Frances Bean Cobain, Courtney Love, and Kurt Cobain at the 1993 MTV Video Music Awards.

Kevin Mazur Archive/WireImage

Nirvana frontman Kurt Cobain and Courtney Love met in a nightclub in 1990 and got married just a few months after meeting.

At the time, Nirvana was at the height of its popularity. The couple became pregnant with daughter Frances Bean a few months into their marriage, during which time they tried to get clean from drugs. 

Their relationship ended in tragedy when Cobain died in 1994 at 27 years old. His death was determined a suicide.

"He is considered to be the rock star who didn't want fame, the weak pathetic guy who was taken over by this controlling female, and yadda yadda," Love told Loudwire in 2015. "He's a hard act to follow. I love him and I always will." 

David Bowie and supermodel Iman met in 1990.
david bowie iman
David Bowie and model Iman in 1990.

Ron Galella/Ron Galella Collection/Getty Images

David Bowie and Iman met in 1990 at a dinner party, where it was apparently love at first sight for the "Rebel Rebel" singer. 

"My attraction to her was immediate and all-encompassing," he told Hello! magazine in 2000. "I couldn't sleep for the excitement of our first date. That she would be my wife, in my head, was a done deal."

The pair married two years after meeting. Iman later said that they fell in love with who they were to each other behind the scenes. 

"I didn't want to get into a relationship with somebody like him," she told The Guardian in 2004, according to Biography. "But as I always said: I fell in love with David Jones. I did not fall in love with David Bowie. Bowie is just a persona. He's a singer, an entertainer. David Jones is a man I met."

The pair kept their marriage and relationship relatively out of the spotlight after Bowie gave up touring in 2004. On January 10, 2016, he died at the age of 69 from liver cancer.

"I will never remarry," she told Porter magazine afterward. "I mentioned my husband the other day with someone, and they said to me, 'You mean your late husband?' I said, no, he is always going to be my husband."

David and Victoria Beckham tied the knot in 1999 and are still going strong.
David and Victoria Beckham
David and Victoria Beckham sported matching haircuts in 1999.

Dave Hogan/Getty Images

David and Victoria Beckham met in 1997 when she was well known as "Posh Spice" and Beckham was reaching international fame for Manchester United. In fact, it was the team that brought them together.

"Yes, love-at-first-sight does exist," Victoria told British Vogue in 2016. "It will happen to you in the Manchester United players' lounge — although you will get a little drunk, so exact details are hazy."

The pair got engaged in 1998 and wed a year later in a lavish ceremony in Ireland. Over their decades of marriage, David has reportedly gifted Victoria 14 different engagement rings, according to W Magazine

They have now been married for 25 years and share four children: Brooklyn Beckham, 25; Romeo James Beckham, 22; Cruz Beckham, 19; and Harper Seven Beckham, 13.

Justin Timberlake and Britney Spears became the ultimate pop power couple when they began dating in 1998.
Justin Timberlake and Britney Spears
Justin Timberlake and Britney Spears in 2000.

Dave Hogan/Getty Images

While Justin Timberlake and Britney Spears' relationship didn't reach superstar status until the early 2000s, they began dating in the late '90s, years after meeting on the set of "The Mickey Mouse Club."

"When people [in the public] get too personal, it bothers me. But I'm not ashamed at all to say that I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough. He's everything," she told The Guardian in 2001. "It is a deeper love now than when I was younger. Like, we've gone through so much together and we've known each other since we were 12 years old. We know each other inside and out."

Britney and Justin broke up in 2002, not long after cementing themselves as an iconic power couple.

In 2021, Timberlake apologized for speaking derogatorily about Spears in an interview and for not speaking out during the "Free Britney" movement concerning her conservatorship. He also addressed the controversy over his infamous Super Bowl performance with Janet Jackson, who was ridiculed in the press after a wardrobe malfunction on stage.

"I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed," Timberlake said in an Instagram post. "Because of my ignorance, I didn't recognize it for all that it was while it was happening in my own life but I do not want to ever benefit from others being pulled down again."

Read the original article on Business Insider

Photos from Walmart's boom in the 1990s show how the retail chain took over the world

4 February 2025 at 09:11
The exterior of a Walmart store in Virginia.
A Walmart store in Virginia.

James Leynse/Corbis via Getty Images

  • The first Walmart store opened in 1962 and it was the No. 1 retailer in the US by 1990.
  • Photos show customers shopping at Walmart during the chain's boom in the '90s.
  • Walmart also expanded into China, Canada, and the UK in the 1990s.

Sam Walton opened the first Walmart store in Rogers, Arkansas, in 1962. By 1980, the retail chain operated 276 locations and achieved $1 billion in sales each year. By 1990, Walmart became the No. 1 retailer in the US.

The big-box brand has continued to dominate, marking its 60th anniversary in 2022 and earning $648 billion in revenue in the fiscal year 2024, according to its latest earnings report.

Photos from Walmart's booming business in the 1990s show the retail chain's rapid growth.

A representative for Walmart did not respond to a request for comment.

Walmart used to have a dash in its name and logo.
A Walmart parking lot in the 1990s.
A Walmart store in Naperville, Illinois.

Ralf-Finn Hestoft/Corbis via Getty Images

Walmart previously used a Western-inspired logo font called "Font Frontier Logo," then switched to bold block letters in 1981.

In 1992, Walmart replaced the dash with a star.
The exterior of a Walmart store in Virginia.
A Walmart store in Virginia.

James Leynse/Corbis via Getty Images

Walmart eventually got rid of the hyphen altogether in 2008.

In the 1990s, Walmart customers were welcomed to stores by "people greeters."
A Walmart employee in the 1990s wearing a vest that reads "Our people make the difference."
A Walmart employee in the 1990s.

Leynse/Corbis via Getty Images

In 2019, Walmart eliminated "people greeter" positions in about 1,000 stores and replaced them with "customer hosts," an expanded role that included checking receipts and processing refunds.

The store's "Always" marketing slogan was relatively new, having been introduced in 1989.
A woman with two children shops at a Walmart store.
Walmart stores offer savings.

Ralf-Finn Hestoft/Corbis via Getty Images

Since the 1970s, Walmart has followed its "every day low prices" strategy, or EDLP, which offers lower prices on products year-round rather than only during special sales or promos.

In 2008, the "Always" slogan was updated to its current iteration, "Save money. Live better."

In 1991, a roll of Sparkle paper towels cost 67 cents at Walmart.
Customers shop at Walmart in the 1990s.
Customers at Walmart in the 1990s.

Ralf-Finn Hestoft/Corbis via Getty Images

In 2025, a two-pack of Sparkle paper towels costs $2.97 at Walmart, or about $1.49 per roll.

Kathie Lee Gifford, then the cohost of "Live! with Regis and Kathie Lee," launched a Walmart clothing line in 1995.
A Kathy Lee Gifford line of clothing at Walmart in the 1990s.
Kathie Lee Gifford's clothing line at Walmart.

James Leynse/Corbis via Getty Images

Walmart's growth was not without controversy.

Gifford and Walmart came under scrutiny when National Labor Committee director Charles Kernaghan testified in a 1996 congressional hearing that Gifford's clothing line was produced by child laborers in sweatshops in Honduras.

"I immediately called Walmart and said this is obscene if this is happening," Gifford said on an episode of "Live! With Regis and Kathie Lee." "They said, 'That happened months ago, we found out about it and took care of it.'"

Gifford later testified before the House Foreign Affairs Subcommittee on International Operations and Human Rights to advocate for better oversight of working conditions to prevent child labor.

"I believe this committee has the means to formulate real and substantive change as to how garments are made for the American consumer," she told lawmakers.

The incident sparked increased awareness of and advocacy for corporate responsibility policies. In subsequent years, Walmart also adopted new standards focused on ethical manufacturing and sustainability abroad.

The chain became a premier Black Friday and holiday shopping destination.
Black Friday at Walmart in the 1990s.
Black Friday at Walmart.

Daniel Hulshizer/AP

On Black Friday in 1998, customers lined up outside Walmart stores at 3 a.m. to secure popular '90s toys such as Furbies.

As Walmart grew into the largest and most profitable retailer in the world, its shareholders meetings became star-studded events.
A 1992 Walmart shareholders meeting.
Helen Walton, the widow of Walmart founder Sam Walton, at the 1992 Walmart shareholders meeting in Little Rock, Arkansas.

Danny Johnston/AP

Celebrity guests at Walmart's shareholders meetings included Reba McEntire, Chet Atkins, Lee Greenwood, and Bill and Hillary Clinton, when they were the governor and first lady of Arkansas. The company also invited employees from across the US.

The 1992 shareholders meeting featured a crowd of 15,000 audience members, AP reported.

Walmart expanded into Canada, China, and the UK in the '90s, cementing the brand as a global mainstay.
A Walmart in Beijing, China.
A Walmart in Beijing.

Cancan Chu/Getty Images

Walmart acquired 122 Woolco stores in Canada in 1994, opened its first locations in China in 1996, and acquired Asda in the UK in 1998.

As of 2025, Walmart operates 10,600 stores in 19 countries with 2.1 million employees worldwide, according to its official website.

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The most infamous crime stories of the '90s

3 December 2024 at 08:23
John and Patsy Ramsey, the parents of JonBenet Ramsey, meet with a small selected group of the local Colorado media after four months of silence in Boulder, Colorado on May 1, 1997. Patsy holds up a reward sign for information leading to the arrest of their daughter's murderer. Their 6-year-old daughter was found dead on Christmas night 1996.
John and Patsy Ramsey in May 1997.

Helen H. Richardson/The Denver Post/Getty Images

  • Throughout the '90s, there were crime stories that shocked the world. 
  • In 1996, 6-year-old pageant queen JonBenét Ramsey was found dead in the basement of her own home.
  • Twenty-eight years later, the case remains unsolved, though there are theories about what happened.

Although the '70s and '80s were known for infamous serial killers, the 1990s also saw some horrific crimes that shocked the nation.

Among those cases was the 1996 murder of 6-year-old JonBenét Ramsey in Boulder, Colorado. She was reported missing by her parents on the morning of December 26, and she was found dead in the basement of her home later that same day.

Twenty-eight years later, it remains unclear exactly what happened to JonBenét, but her mysterious death captivated the nation for years, leading to podcasts, TV movies, an upcoming limited series on Paramount+, and multiple true-crime series, including the most recent Netflix series "Cold Case: Who Killed JonBenét Ramsey," which premiered in November.

From mass shootings to heartbreaking celebrity deaths, here are some of the most unforgettable crimes of the '90s. 

Infamous serial killer Jeffrey Dahmer murdered his last victim and was caught in 1991.
Jeffery Dahmer
Jeffrey Dahmer.

Allen Fredrickson/REUTERS

On May 27, 1991, an injured 14-year-old boy was seen running through the streets, reported The New York Times.

When police responded, Jeffrey Dahmer told the officers the boy was his lover and that they had a flight. After the officers returned the boy to Dahmer and escorted them both home, Dahmer killed him. Dahmer went on to kill four more men, bringing his total number of murder victims to 17, per the Times.

In July of that year, Tracy Edwards, a 32-year-old Black man, was seen walking the streets with his hands handcuffed. He brought police officers to Dahmer's house, which is where he said he was cuffed. When the officers entered the house, they saw photographs of body parts lying around. Dahmer was arrested on the spot.

Dahmer was found guilty and sentenced to 15 consecutive life terms. He was killed in prison by a fellow inmate in 1994.

Dahmer remains one of the nation's most disturbing serial killers. The chilling case became the subject of a 2017 movie, "My Friend Dahmer," based on a graphic novel, and the 2022 Netflix miniseries "Dahmer — Monster: The Jeffrey Dahmer Story."

Pablo Escobar, the Colombian drug lord, was shot in 1993 when he was on the run from authorities.
Pablo Escobar
Pablo Escobar.

AP

Pablo Escobar became one of the richest people in the world in the late '80s and early '90s thanks to the cocaine trade that he controlled out of Colombia.

His Medellín Cartel was responsible for 80% of the cocaine sent to the US, leaving thousands dead, per The Wall Street Journal. He became a target for the US and authorities in Colombia, so he went on the run. 

On December 2, 1993, Escobar attempted to escape the authorities by running across rooftops in Medellin, but he was killed in a shoot-out. His death marked the end of the country's reign on cocaine.

When Nicole Brown Simpson and Ron Goldman were found dead in 1994, OJ Simpson was arrested, sparking the trial of the century.
oj simpson
OJ Simpson at his trial.

AP Photo/Sam Mircovich/Pool

On June 12, 1994, Nicole Brown Simpson was stabbed to death outside her Los Angeles home with her friend Ron Goldman.

Her ex-husband, NFL star OJ Simpson, quickly became a prime suspect. He was arrested and charged with the two murders after leading police on a televised 60-mile car chase through Los Angeles. When he finally surrendered in his home, Simpson pleaded "absolutely, 100 percent not guilty."

The trial itself became a media frenzy, as Simpson famously tried on the gloves that were left at the murder scene.

On October 3 the following year, Time wrote that over 150 million people (57% of the US population at the time) tuned in to hear the verdict. After just two hours of deliberations, Simpson was found not guilty.

The murders of Nicole Brown Simpson and Ron Goldman are still unsolved. OJ Simpson died in April 2024.

In 1994, Gary Ray Bowles went on an eight-month killing spree and became known as the I-95 Killer.
Gary Ray Bowles
Gary Ray Bowles.

Florida Department of Corrections

Gary Ray Bowles killed his first victim, John Hardy Roberts, in Daytona Beach in 1994. From there, he murdered five more gay men along Interstate 95 in Maryland, Georgia, Atlanta, and Florida.

At one of his crime scenes, Bowles left a probation document, and he was caught on surveillance camera taking money out of the victim's account. When he was finally caught, he was convicted of three out of the six murders. He was executed by lethal injection in 2019.

While at the height of her career, Latin singer Selena was killed in March 1995.
selena quintanilla
Selena.

Barbara Laing / Contributor/Getty Images

The month before her murder, Selena Quintanilla (known mononymously as Selena) was at the height of her career, performing for 60,000 people at the Houston Astrodome.

Her album "Amor Prohibido" was nominated at the Grammys for best Mexican-American performance. She was also working on an English album that she hoped would transform her into a crossover hit. By all accounts, she was poised to become the next Gloria Estefan. 

But everything changed in March 1995.

The year prior, she made Yolanda Saldívar the manager of the Selena fan club and put her in charge of the singer's boutiques.

Selena quickly noticed that there were money discrepancies and missing documents with both those businesses. Over the course of a couple of months, Selena confronted Saldívar about the missing documents. Ultimately, those conversations ended with Saldívar shooting Selena after they met at a hotel room, The New York Times reported. She was 23 years old. 

Saldívar was convicted and sentenced to life in prison with no possibility of parole for 30 years. She is currently in a Texas prison and will be eligible for parole in March 2025.

Meanwhile, Selena's song "Dreaming of You" debuted after her death and reached the No. 1 spot on the US Billboard 200 charts. 

In 1995, Timothy McVeigh parked a truck filled with explosives in front of a federal building in Oklahoma City, killing 168 people.
oklahoma city bombings
Oklahoma City bombing.

AP

On April 19, 1995, Timothy McVeigh rented a Ryder truck with agricultural fertilizer, diesel fuel, and other chemicals inside.

He parked the truck outside the Alfred P. Murrah Federal Building in Oklahoma City and walked to a getaway car. When the bomb went off, it destroyed the building and killed 168 people. Among them, 19 were children, CNN reported.

When the FBI found a rear axle from the truck in the rubble, they quickly traced the piece back to McVeigh, a former US Army. From there, the evidence continued to build against McVeigh: He had traces of chemicals on his clothing, and he even jotted down notes about the bombing beforehand. The FBI also found that two other men knew about the bombing plot and helped him devise the plan.

McVeigh was convicted on 15 counts of murder and was sentenced to death. He was executed in 2001.

A bomb went off at the Summer Olympic Games in Atlanta in 1996, leading to the deaths of two people.
atlanta olympics
The Atlanta Centennial Olympic Park.

Michael Green/ AP

On July 27, 1996, police received an anonymous phone call telling them a bomb would go off in 30 minutes at the Centennial Olympic Park in Atlanta.

As the location was being evacuated, the bomb went off early. A woman was killed, and a cameraman who was rushing to the scene also suffered a fatal heart attack, CNN reported. More than 100 more were injured.

At first, security guard Richard Jewell, who found the backpack that held the bomb, was identified as a suspect. Eventually, Jewell was cleared of any wrongdoing. This series of events was covered in the 2019 film "Richard Jewell."

The crime went unsolved until 1998 when a series of bombings in the South linked Eric Robert Rudolph to the Olympic bombings.

He eluded police for several more years and was eventually arrested in 2003. Rudolph was convicted and was sentenced to four consecutive life sentences.

On September 13, 1996, Tupac Shakur was killed in a drive-by shooting in Las Vegas. His rival, the Notorious BIG, was murdered in a similar way six months later.
Tupac Shakur in 1994
Tupac Shakur pictured in 1994.

Ron Galella/Ron Galella Collection via Getty Images

Tupac Shakur made a name for himself as an acclaimed rapper whose music fought against injustice toward Black Americans. Shakur made hit after hit, creating four platinum albums throughout his career. 

But on September 7, 1996, he was seen leaving the MGM Grand Hotel in Las Vegas after getting into a fight. Shakur was in the passenger seat of a car when another car pulled up beside him at a red light, and 13 shots were fired.

He died at the hospital on September 13. 

Since Shakur's death, seven albums have been released under his name, making him one of the best-selling artists of all time.

Some believed his biggest rival, rapper Christopher Wallace (aka Biggie, Biggie Smalls, or the Notorious BIG), was behind his murder, but he denied any involvement.

On March 9, 1997, Biggie was killed, also while waiting at a red light.

Over the years, there have been many theories about what happened to the men.

In September 2023, Duane Davis (also known as Keffe D) was arrested in connection with Shakur's murder, 27 years after Shakur's death. Davis pleaded not guilty in November 2023, NPR reported. His trial was originally scheduled to start in June 2024 but was postponed to November, and then delayed again to March 2025, per Rolling Stone.

JonBenét Ramsey, a 6-year-old beauty queen, was murdered in 1996, and the case remains open today.
The grave of JonBenet Ramsey,
The grave of JonBenét Ramsey.

Chris Rank/Sygma/Getty Images

On December 26, 1996, Patsy Ramsey called the police saying her daughter, JonBenét, was missing and that a three-page ransom note was left on the staircase from a kidnapper who demanded $118,000.

JonBenét's body was found in the basement of the Ramsey home later that day.

From the start, the murder investigation was problematic.

John Ramsey had picked up and moved JonBenét's body out of the basement after she was found. John and Patsy were also interviewed together by investigators, which is not typical police procedure. Since the parents gave inconsistent accounts of what happened that night, the public pointed fingers at them

In 2006, the Ramseys were cleared of any wrongdoing because of advancements in DNA evidence. To this day, no one has been charged with the death of JonBenét, though the latest Netflix series puts forth some theories.

Famous designer Gianni Versace was assassinated by a serial killer in 1997.
versace murder
The mansion where Versace was shot.

Alan Diaz/ AP

On July 15, 1997, Gianni Versace arrived at his mansion in Miami and was shot by Andrew Cunanan on the front steps.

Before the murder, as reported by Harper's Bazaar, Cunanan was already on the FBI's Most Wanted List after a killing spree where he murdered four men: Jeffrey Trail, David Madson, Lee Miglin, and William Reese.

Once Versace's murder made headlines, a nationwide manhunt ensued.

It all came to a head at a houseboat that Cunanan broke into. As police closed in on him, Cunanan killed himself using the same gun he had used on three of his victims.

To this day, it's unclear what his motives were, though an attempt to explore his headspace was shown in "The Assassination of Gianni Versace: American Crime Story" in 2018.

The famous comedian Phil Hartman was murdered by his wife in 1998.
Phil Hartman
Phil Hartman.

Ron Galella/Getty Images

Phil Hartman was famous for the eight seasons he spent as a cast member on "Saturday Night Live." While on the show, he was known for his impression of President Bill Clinton. He also went on to play a news anchor in the sitcom "NewsRadio." 

But the comedian may be best known for his tragic death. On May 28, 1999, Hartman's wife, Brynn, shot the comedian as he lay in bed. As the police arrived at the Los Angeles home, they heard a gunshot as Brynn killed herself.

On April 20, 1999, two students opened fire on their classmates at Columbine High School, killing 13 people and wounding 20 others.
columbine high school
Columbine High School.

Getty Images/Steve Corbis

Around 11 a.m., Dylan Klebold and Eric Harris walked into Columbine High School in Colorado wearing trench coats and placed a bomb in the school cafeteria.

They walked back outside to their cars and waited. When the bombs didn't go off, they went back into the school armed with guns and shot their classmates. They killed 12 students and one teacher during their rampage. A little after noon, the pair killed themselves. 

Although the motive of the shooters is still unknown, the incident became the most deadly school shooting in history at the time. It also sparked the national conversation around gun control and gun violence, which is still raging to this day.

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