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.
Brad Pitt and Jennifer Aniston
This couple became 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.
Kurt Cobain and Courtney Love
After meeting in 1990, this tumultuous couple became 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.
Gwen Stefani and Gavin Rossdale
The No Doubt frontwoman and Bush’s lead singer were a rock ‘n’ roll dream team in the late ’90s. They were known for their edgy style and shared a love for music. Their relationship blossomed from collaboration to romance, captivating fans with their unique dynamic and swooning all of our hearts.
Tom Cruise and Nicole Kidman
Cruise and Kidman were the ultimate power couple. 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. They would defy the Hollywood odds and stay together for eleven long years.
Drew Barrymore and Tom Green
This unconventional couple 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.
Reese Witherspoon and Ryan Phillippe
This charming couple became one of Hollywood’s most beloved duos after meeting on the set of Cruel Intentions. Their picture-perfect romance captivated fans, but their marriage ended in 2007, breaking all of our hearts.
Winona Ryder and Johnny Depp
One of our favorite couples captured young love in the early ’90s after meeting on the set of Edward Scissorhands. Their deep devotion was marked by public affection and iconic moments, leaving a nostalgic imprint on pop culture.
Cameron Diaz and Matt Dillon
This Hollywood couple was known for their chemistry and charm. They first met while filming There’s Something About Mary. Their fun-loving dynamic was super fun to watch on all the red carpets while it lasted.
