
Memory lane
Not all Hollywood relationships were built to last. Still, all of these duos from the ’90s will live in infamy. Many of them met on the set of some of our favorite movies and shows of the time. Read on if you want to take a nostalgic trip down memory lane.
Broken heart
Julia Roberts was America’s Sweetheart in the 90s, while Kiefer Sutherland was a straight up bad boy. The pair met while filming Flatliners, and were pretty much engaged moments after they stopped filming. A tabloid sensation from the jump, the couple was set to marry in 1991 but then things went off the rails. Days before the ceremony, Roberts called off the wedding and flew to Ireland with Jason Patric, leaving Sutherland with nothing but a broken heart.
Hollywood romance
Brad Pitt and Jennifer Aniston were the epitome of Hollywood romance when they tied the knot in 2000, capturing the media’s attention throughout the late 90s. Their undeniable chemistry made them one of the most photographed couples of the decade. Of course, our hearts were shattered when Pitt left Aniston in 2044 for Angelina Jolie, whom he met while filming Mr. & Mrs. Smith.
Tragic death
After meeting in 1990, Kurt Cobain and Courtney Love were immediately the embodiment of rock ‘n’ roll rebellion in the 90s. Their passionate relationship, marked by intense highs and lows, drew intense media scrutiny and remains a powerful symbol of the grunge movement. The couple remained together until Cobain’s tragic death in April 1994.
Call it quits
Long before she was the GOOP queen, Gwyneth Paltrow was in a majorly high-profile romance with Ben Affleck throughout the late 90s. A classic Hollywood story, they met at a party in 1997, hit it off, and they were dating by the time they co-starred in Shakespeare in Love. They were all smiles for the camera, but behind the scenes their relationship was on thin ice. The couple ended things in 2000, the perfect time for any 90s couple to call it quits.
Dream team
Gwen Stefani, the No Doubt frontwoman, and Gavin Rossdale, Bush’s lead singer, were a rock ‘n’ roll dream team in the late 90s. The couple met on tour while they were both on the top of the world with hits like “Glycerine” and “Don’t Speak” and immediately became a media fixture. Honestly, they were so hot together that when they announced their split in 2015.
Eleven long years
Tom Cruise and Nicole Kidman were the ultimate power couple in the 90s. They married shortly after meeting on the set of Days of Thunder and would go on to film numerous films together, including leaving all of us drooling in Eyes Wide Shut. The couple defied the Hollywood odds and stayed together for eleven long years.
Unconventional couple
Drew Barrymore and Tom Green were an unconventional couple who made waves in the late ’90s with their playful relationship and spontaneous spirit. You might not remember the name Tom Green unless you were around in the 90s, but he was a famous comedian then. Their brief romance showcased a fun-loving dynamic that >captured the attention of fans and tabloids alike.
Most beloved duos
Reese Witherspoon and Ryan Phillippe were a charming couple who became one of Hollywood’s most beloved duos after meeting on the set of Cruel Intentions in the late 90s. Their picture-perfect romance captivated fans, but their marriage ended in 2007, breaking all of our hearts.
Favorite couples
One of our favorite couples captured young love of the early 90s, Winona Ryder and Johnny Depp, got together after meeting on the set of Edward Scissorhands. Looking back now, it’s clear that we were all transfixed by their goth chic, but they were so young that it’s clear they were never going to work out. If nothing else, this relationship gave us the classic “Winona Forever” tattoo.
Power couple
In the late 90s, Jennifer Love Hewitt was everywhere. She got her start on Party of Five, and transitioned to full scream queen status with her role in I Know What You Did Last Summer. Carson Daly was the king of MTV’s Total Request Live. I makes perfect sense that they became a power couple for the MTV set, gracing red carpets for years. Unfortunately, their romance was not built to last with Daly moving on to date Tara Reid once he and Hewitt split.
