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.
#Hollywood
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Entourage
One movie star, his three guys from Queens, and the super-agent screaming them all toward the top. Entourage was HBO's mid-2000s fantasy of Hollywood — Maseratis, premieres, Malibu — and Jeremy Piven's Ari Gold turned "let's hug it out" into the decade's boardroom catchphrase. Aspiration as entertainment, and for a few years it absolutely worked.
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.
Leonardo DiCaprio
The floppy-haired heartthrob whose face covered every bedroom wall and Tiger Beat cover after Titanic. Before he was an Oscar-winning elder statesman of film, '90s Leo was pure teen-idol "Leo-mania."
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.