Until the 88th Academy Awards in 2016 Leonardo DiCaprio was the laughing stock of Hollywood. The famous star of Titanic and The Great Gatsby was nominated five times for his acting performances but missed the golden statue four times.
DiCaprio was first nominated before the age of twenty in 1993 for What’s Eating Gilbert Grape with Johnny Depp and Juliette Lewis. This is his only Academy Award nomination as a supporting actor but Tommy Lee Jones accepted the statuette for his role in The Fugitive.
The second nomination for Leo came 12 years later for his depiction of film mogul Howard Hughes in Martin Scorsese‘s The Aviator. However he lost to Jamie Foxx who played the blind singer Ray Charles in the biopic Ray. Actors who play existing people always have an advantage at the Academy Awards but in this case both actors played historic people.
Third time lucky, but not for Leonardo DiCaprio who got nominated for playing an Australian smuggler in Blood Diamond in 2007. Although this is without a doubt one of his best performances to date he lost to Forest Whitaker who played Idi Amin in the biopic The Last King of Scotland.
Seven years later, DiCaprio was once more nominated for a part in a Scorsese movie. This time he played drug crazy stock broker Jordan Belfort in The Wolf of Wall Street. An excellent performance but he was outshined by Matthew McConaughey in Dallas Buyers Club. Funny detail: McConaughey also had a small role as Belfort’s mentor in The Wolf of Wall Street.
On 28 February 2016 DiCaprio finally won his more than deserved Oscar for Best Actor for his role as bear hunter Hugh Glass in The Revenant by Alejandro G. Iñárritu. This year Leo even beat Bryan Cranston as Dalton Trumbo and Michael Fassbender as Steve Jobs. With this victory Leonardo DiCaprio finally has an equal amount of Oscars as these well known people.
Marshall Mathers aka Eminem did not win the Academy Award for Best Actor but for Best Original Song for his hit Lose Yourself. The song was featured in 8 Mile, a movie in which Eminem starred. In 2002 Eminem became the first hip hop artist to win an Oscar.
The Boss never acted but won an Academy Award for Best Original Song for the beautiful track Streets of Philadelphia. This ballad appeared on the soundtrack of the movie Philadelphia starring Tom Hanks and Denzel Washington. The deceased Whitney Houston announced the winner instead of winning the Oscar herself like her character in the flop The Bodyguard.
English singer and drummer Phil Collins liked to act in the music videos for his band Genesis in the eighties and nineties. His Oscar nominations however never celebrated his acting qualities. In 1984 Collins was nominated for the title song to Against All Odds with Jeff Bridges but lost to Stevie Wonder‘s I Just Called to Say I Love You. The same year Ghostbusters was nominated and Footloose was nominated twice with the theme song and Let’s Hear It For the Boy.
The late singer and performer Prince (né Prince Rogers Nelson) acted in the 1984 movie Purple Rain. Anyone who has actually seen the movie understands why The Artist Formerly Known As Prince did not receive a nomination for Best Actor from the Academy. The movie Purple Rain did however earn His Purple Highness an Oscar for Best Original Song Score. Little Purple Riding Hood was given the award by popular movie duo at the time, Michael Douglas and Kathleen Turner who played together in The War of the Roses and in Romancing the Stone.
In 2014 Pharrell Williams known for The Neptunes and for wearing sillier hats than Jay Kay from Jamiroquai won the Oscar for Best Original Song. His catchy track Happy which featured in the minions movie Despicable Me 2 earned him the golden statuette before Leonardo DiCaprio owned one.
Singer and widow of Sonny Bono, Cherilyn Sarkisian better known as Cher is one of the few performers in the list who didn’t win the Oscar for Best Original Song. Cher who played in the disappointing movie The Witches of Eastwick but won the Academy Award for Best Actress for her role in the 1987 romantic comedy Moonstruck starring Nicolas Cage.
The 1988 Best Actress nominations were announced by legend Paul Newman and comedian Chevy Chase. It’s hard to believe she actually won from Glenn Close, Meryl Streep and Holly Hunter.
“What the hell is Lionel f*cking Richie doing in this list? Are you freaking kidding me?” I can hear you think. Well, I kid you not! The super slick ballad singer did win the Academy Award for Best Original Song with his track Say You, Say Me. This tearjerker was featured in the forgotten 1985 movie White Nights.
Sir Elton John, the British singing pianist was nominated three times in the same year. In 1995, three songs by Reginald Dwight (you didn’t believe John was his real last name, did you?) from the Disney movie The Lion King were nominated. Hakuna Matata, Circle of Life and Can You Feel the Love Tonight were nominated but only one song could win the Oscar for Best Original Song and it was the latter. The announcement was made by the Italian Stallion, Sylvester Stallone.
Three 6 Mafia
Four years after Eminem paved the road for rap artists in 2002, the hip hop act Three 6 Mafia surprisingly won the Academy Award for Best Original Song for the movie Hustle & Flow. It’s hard to imagine the Academy let a song called It’s Hard Out Here for a Pimp win an Oscar instead of the great Dolly Parton.
The four boys from Liverpool managed to win the Academy Award for Best Original of Adaptation Score for the documentary Let It Be at the Oscars in 1971. Not an easy task if you know the band broke up in 1970. It’s no surprise none of the Liverpudlians attended the ceremony. Legendary producer and composer Quincy Jones accepted the statuette on behalf of The Beatles and gave one of the shortest acceptance speeches in Oscar history.