Brad Pitt
The reigning heartthrob of the 1990s — the drifter who stole Thelma & Louise, the golden boy of Legends of the Fall, the detective screaming "what's in the box?", and finally Tyler Durden. No face was taped inside more mid-90s lockers.
Brad Pitt's breakout took only a few minutes of screen time: as J.D., the charming drifter in Thelma & Louise (1991), his scene with Geena Davis has been cited as the moment that defined him as a sex symbol. He spent the next few years proving he was more than that — A River Runs Through It (1992) recast him as a serious leading man (though Pitt himself, feeling the pressure, later called it one of his weakest performances).
Then came the run. In 1994 alone he was the vampire Louis in Interview with the Vampire — panned by many critics but a winner of two MTV Movie Awards — and Tristan Ludlow in Legends of the Fall, which earned his first Golden Globe nomination. In 1995 he went dark: Se7en, opposite Morgan Freeman and Kevin Spacey, earned $327 million at the international box office, and his twitchy turn as Jeffrey Goines in 12 Monkeys won the Golden Globe for Best Supporting Actor and brought his first Academy Award nomination. That same year People crowned him Sexiest Man Alive — a title he'd collect again in 2000. Off-screen, his engagement to Gwyneth Paltrow (they dated from 1994 to 1997) was tabloid wallpaper for the whole mid-decade.
He closed the 90s with the role that aged best: Tyler Durden in Fight Club (1999), a box-office disappointment that became a cult phenomenon after its 2000 DVD release. By then the decade's golden boy was Hollywood's biggest star, and his July 29, 2000 wedding to Friends star Jennifer Aniston in Malibu fused the two biggest celebrity currencies of the era into tabloid royalty.
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Fight Club
David Fincher's anti-consumerist fever dream — Edward Norton's insomniac narrator, Brad Pitt's Tyler Durden, and a basement club with rules you weren't supposed to talk about. It bombed with critics split down the middle and underwhelmed in theaters, then the DVD turned it into the defining cult movie of its generation.
Tom Cruise
The megawatt grin that ruled the 90s box office. From Days of Thunder through Jerry Maguire to Magnolia, Tom Cruise spent the decade as Hollywood's defining leading man — and spent 1996 building his own action franchise by dangling from a wire as Ethan Hunt.
Friends
NBC's ten-season juggernaut turned Central Perk into a real place and gave six 20-something New Yorkers the kind of friendship every 90s kid wanted. Rachel's haircut, Monica's apartment, Ross and Rachel's will-they-won't-they, and that theme song — an inescapable cultural monument that redefined the sitcom.
Julia Roberts
The megawatt smile that owned the 90s box office. From Pretty Woman through Notting Hill and Runaway Bride, Julia Roberts was the romantic-comedy lead every studio wanted and every video store shelved face-out — then she capped the run by winning the Oscar as Erin Brockovich.