It’s hard enough to become a global success at any one thing. Music demands charisma, presence, and the ability to connect with millions. Acting demands nuance, discipline, and the ability to disappear into someone else entirely.
Very few people have truly mastered both.
In fact, only five artists in modern entertainment history have achieved the rare double of scoring a US Number 1 single and winning an Academy Award for acting.
On this week’s Fast Forward podcast, GB and AJ – carrying on from the Rewind episode where they looked at megastar David Bowie in Labyrinth – talked about the good and the bad of singers who went into the movies and discuss The Big 5. You can listen to the full show in the player above or wherever you listen (Apple Podcasts, Spotify, Amazon Music and more)
Here are the five who pulled it off...
Frank Sinatra
Before crossover careers were even a concept, Frank Sinatra was already doing it.
Rising to fame as one of the biggest recording artists of the 1940s, Sinatra could have stayed comfortably in music. Instead, he pivoted to film and proved he was far more than just a voice.
His performance in From Here to Eternity (1953) earned him the Academy Award for Best Supporting Actor, revitalising his career and cementing his legitimacy in Hollywood.
Sinatra didn’t just dabble in acting. He became a leading man, starring in over 60 films.
He set the template. Every crossover success that followed owes something to Sinatra proving it could be done.
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Barbra Streisand
Barbra Streisand owned both worlds. After dominating Broadway and the charts, she transitioned seamlessly into film, winning the Academy Award for Best Actress for Funny Girl (1968).
But what separates Streisand is control. She directed, produced and shaped her projects, including Yentl.
With multiple Grammys, Oscars, and decades of success, she’s one of the few artists who never had to choose between industries.
She proved you can lead creatively in both music and film and win at the highest level in each.
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Cher
Cher’s career is built on reinvention but started acting and singing at the same time.
Already a global music icon, throughout the 1980s her acting was escalating, culminating in an Academy Award win for Best Actress in Moonstruck (1987).
What’s remarkable is how she overcame early scepticism. Critics didn’t initially take her seriously as an actor but she kept pushing until they had no choice.
Meanwhile, she continued producing chart-topping hits across multiple decades.
She turned doubt into credibility and became one of the most versatile entertainers ever.
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Jamie Foxx
Some will say Jamie Foxx is the most naturally gifted all-rounder on this list.
Starting in comedy, moving into acting, and maintaining a successful music career, Foxx has always operated across multiple lanes.
But it was his performance as Ray Charles in Ray (2004) that defined everything. He embodied the role, winning the Academy Award for Best Actor.
At the same time, his music career delivered major hits, including a US Number 1 single.
He represents the modern multi-hyphenate as someone equally credible in every arena he steps into.
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Will Smith
Will Smith’s journey might be the most visible of them all.
From chart-topping success as The Fresh Prince to global superstardom in The Fresh Prince of Bel-Air, he made the transition into film look effortless.
Then came blockbuster dominance: Independence Day, Men in Black, Ali, The Pursuit of Happyness.
Finally, he secured the Academy Award for Best Actor for King Richard (2021), completing the rare double.
Regardless of what you think of him post-slap, he doesn’t just slip onto the end of this list as a modern Frank, Cher, Barbra stat-filler. He did it by becoming one of the biggest movie stars on the planet.
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Who’s Next?
Modern stars like Lady Gaga are getting close. Others have shown flashes.
But joining this group isn’t about potential, it’s about proof. And probably luck.
Until someone else earns both a No.1 single and an Oscar for acting, this remains one of the most exclusive clubs in entertainment history.
And right now, it still only has five members.
You can listen to more on this discussion of Singers in Movies by checking out the podcast wherever you listen (Apple, Spotify etc). Or at the top of this article where we put a handy player.
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