Pascal grins at the opening of the play Absurd Person Singular in New York. In 2005, he was a theater scene staple, working as both an actor and director before turning to TV gigs.

In 1954, Brando won his first Oscar for his performance in On The Waterfront. That same year, he filmed Guys and Dolls, his first and only musical role.

Roberts accepts the Hasty Pudding Woman of the Year award at a ceremony held at Harvard University. 1997 marked her return to the rom-com genre, with a lead role in My Best Friend’s Wedding.

The actress is photographed arriving at the Lunch Hour premiere party in New York City. She was reportedly considered for a starring role in 1980’s The Shining, but the part eventually went to Shelly Duvall.

In 1988, the actress, pictured here in a still from the movie Tequila Sunrise, also starred in Married to the Mob and Dangerous Liaisons. The latter earned her a Best Supporting Actress Oscar nomination.

The crooner smiles for a studio portrait in Los Angeles. Although he signed with Columbia Records in 1943, Sinatra wouldn’t release his first album until 1946. During this period, he spent significant time performing for troops overseas during World War II.

Washington poses for a headshot in character as Dr. Phillip Chandler on St. Elsewhere. The show, which premiered in 1982 and followed a group of medical interns training at a teaching hospital in Boston, was the actor’s big TV break. It wouldn’t be long until he’d take over the big screen too.

Goldblum celebrates the premiere of The Big Chill at an after-party held at the Beverly Hills Hotel. The actor played a journalist in the movie, which follows college friends who reunite after the death of a member of their group.

Downey is all smiles at the Los Angeles premiere of the comedy Home For The Holidays. That same year, the busy actor starred in Richard III, Mr. Willowby’s Christmas Tree, and Restoration.

Redford rocks a classic turtleneck in a studio headshot. In 1966, the actor starred in films with Natalie Wood and Jane Fonda—and he would go on to collaborate with both actresses several times throughout his career.

A long-locked Pitt, clad in a suede vest (hey, it was the ’90s) attends the Independent Spirit Awards. The actor, coming off of a career-high with his acclaimed performance in A River Runs Through It, followed up the role by playing a serial killer in Kalifornia and a stoner in the cult action film True Romance.

Huston vamps at a party celebrating the opening of the new Fendi boutique on Rodeo Drive. In 1981, the actress was fresh off of a role in The Postman Always Rings Twice, in which her character had a fling with a drifter played by Jack Nicholson, her on-again, off-again boyfriend.

In 1984, Winfrey moved to Chicago to helm AM Chicago—which, at the time, was suffering from low ratings. Within a year, the show became the most popular daytime talk show in the city. And less than two years later, The Oprah Winfrey Show premiered.

Although the singer’s namesake band had already cemented itself in rock history by 1992, Bon Jovi unexpectedly made waves by chopping his signature long hair as part of a new, more mature chapter for the band.

Fawcett shows off her legendary blonde curls at the Golden Globes. A year prior, in 1976, the Charlie’s Angels star posed in a red swimsuit in her backyard, creating a photo that became the bestselling poster of all time of all time.

DiCaprio sports a backwards cap and a John Kerry T-shirt at a New York screening of Going Upriver: The Long War of John Kerry, a documentary about the politician. He also starred in The Aviator that same year.

Nicholson smiles in costume on set of the movie Psych-Out. In 1967, the actor, who was down on his luck after losing out on several roles, tried his hand at screenwriting with the counterculture film The Trip, starring Peter Fonda and Dennis Hopper. His big on-screen break would come in 1969, when he scored a supporting role in Easy Rider—once again, with Fonda and Hopper.

Parker shows off her signature curls backstage at the Academy Awards. Just three years later, the world would meet Sex and the City‘s Carrie Bradshaw.

Newman enjoys a snack while strolling through a California flea market. (Perhaps a precursor to his Newman’s Own culinary empire?) The year before, the actor starred in his first feature film, The Silver Chalice.

Here, Phoenix makes an appearance on MTV’s Total Request Live. His outfit repped two of his upcoming projects: His hat felt very apropos for his role as a Baltimore firefighter in 2004’s Ladder 49, while his Johnny Cash T-shirt got fans excited for his portrayal of the country icon in 2005’s Walk The Line.