In an industry that often celebrates overnight success, the path to an Academy Award can be surprisingly long, even for the most recognizable stars. This list highlights ten A-listers who spent 20 years or more building their careers before finally hearing their name called on Oscar night.
Robert Downey Jr.
Few careers in Hollywood have been as turbulent, or as enduring, as Robert Downey Jr.’s. A former child actor who grew up on film sets, he earned early critical acclaim with his uncanny turn as Charlie Chaplin in “Chaplin,” which brought him his first Academy Award nomination in 1993. For a moment, it seemed like Oscar success might come quickly.
It didn’t. Decades passed, marked by both career setbacks and reinventions, including a scene-stealing, nomination-worthy comedic performance in “Tropic Thunder.” Then, more than 30 years after his first nomination, Downey finally claimed his long-awaited prize, winning Best Supporting Actor for his performance as Lewis Strauss in “Oppenheimer” at the 2024 ceremony.
Helen Mirren
Long before she became Oscar royalty, Helen Mirren was already commanding attention on screen, beginning with her breakout film role in “Age of Consent.” Over the decades that followed, she built a formidable reputation across stage and screen, earning admiration for her range and authority, yet the Academy kept her at arm’s length, offering nominations for performances in “The Madness of King George” and “Gosford Park” without a win.
That changed when she stepped into the role of Queen Elizabeth II in “The Queen,” delivering a performance defined by restraint and precision. At 61, Mirren finally secured the Academy Award for Best Actress, roughly 38 years after her film debut.
Michael Caine
By the time Michael Caine finally heard his name called at the Oscars, he had already spent decades as one of Britain’s most reliable leading men. His first nomination came in 1967 for “Alfie,” a performance that defined his early screen persona, and was followed by further recognition for “Sleuth” and “Educating Rita.” Still, the award itself remained just out of reach.
The breakthrough arrived in 1987, when Caine won Best Supporting Actor for “Hannah and Her Sisters,” more than 20 years after his first nomination. In a twist that has become part of Oscar lore, he wasn’t there to accept it, as he was busy filming “Jaws: The Revenge” at the time.
Jessica Tandy
Unlike many of her peers, Jessica Tandy didn’t follow the typical Hollywood trajectory to Oscar recognition. For decades, she was already a towering figure of the stage, originating the role of Blanche DuBois in “A Streetcar Named Desire” and collecting Tony Awards for productions like “The Gin Game” and “Foxfire.” Film audiences knew her from roles in projects such as “The Birds,” but her greatest mainstream success would come much later.
At an age when most careers have long slowed down, Tandy reached an entirely new level of visibility. Her performance in “Driving Miss Daisy” earned her the Academy Award for Best Actress, making her the oldest winner in that category at 80. Already a recipient of an Emmy and multiple Tonys, the win completed her “Triple Crown” and solidified a legacy that bridged theater prestige and late-career cinematic acclaim.
Al Pacino
For years, Al Pacino seemed destined to be one of the greatest actors never to win an Oscar. He burst onto the Academy’s radar with his supporting role in “The Godfather,” earning his first nomination in 1973, and quickly became a fixture at the ceremony thanks to powerhouse performances in films like “Serpico,” “Dog Day Afternoon,” and “…And Justice for All.” Despite the steady recognition, the award itself remained elusive through the 1970s and 1980s.
By the early 1990s, the narrative around Pacino had shifted from rising legend to overdue icon. That finally changed with “Scent of a Woman,” which earned him the Academy Award for Best Actor in 1993, exactly 20 years after his first nomination.
Judi Dench
Long before Hollywood fully embraced her, Judi Dench had already spent decades building a formidable reputation on the British stage, beginning in the late 1950s. Her early film work, including “The Third Secret,” hinted at her screen presence, but it would take many years before international audiences—and the Academy—caught up with her stature.
That recognition arrived in quick succession late in her career. After earning her first nomination for “Mrs. Brown,” Dench won the following year for her portrayal of Elizabeth I of England in “Shakespeare in Love.” Her performance lasted only minutes on screen, yet it proved unforgettable, securing her the Best Supporting Actress Oscar more than 40 years after her professional debut and marking the beginning of a prolific run of nominations.
Leonardo DiCaprio
There was a time when Leonardo DiCaprio was better known for near-misses than wins at the Oscars. He first caught the Academy’s attention as a teenager with his supporting role in “What’s Eating Gilbert Grape,” earning a nomination at just 19 and setting expectations sky-high for what would follow.
Over the next two decades, DiCaprio delivered a string of acclaimed performances, yet the award itself remained stubbornly out of reach despite multiple nominations. That narrative finally shifted with “The Revenant,” which earned him Best Actor at the 2016 ceremony, closing a 22-year gap between his first nomination and his first win.
Brad Pitt
Awards recognition came in stages for Brad Pitt, whose Hollywood career spans decades of both critical acclaim and commercial success. He first entered the Oscar conversation as an actor with a nomination for “12 Monkeys” in 1996, but like many of his peers on this list, early momentum didn’t immediately translate into a win.
Interestingly, his first Academy Award arrived not for acting, but for producing, when “12 Years a Slave” won Best Picture in 2014. It would take several more years before he claimed an acting trophy, finally winning Best Supporting Actor for “Once Upon a Time… in Hollywood” in 2020, more than two decades after his first nomination and over 30 years into his time in the industry.
