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The musician-to-actor pipeline isn't a modern invention. Frank Sinatra was doing it in the '50s, Barbra Streisand in the '60s. These are the ones who made it look natural.

Lady Gaga
40
A Star Is Born, House of Gucci

Will Smith
57
From Fresh Prince to Ali to King Richard

Ice Cube
56
Friday, Boyz n the Hood, Barbershop

Justin Timberlake
45
The Social Network, Inside Llewyn Davis

Frank Sinatra†
1915-1998
From Here to Eternity, The Manchurian Candidate

David Bowie†
1947-2016
The Man Who Fell to Earth, Labyrinth

Barbra Streisand
84
Funny Girl, A Star Is Born, The Way We Were

Cher
79
Moonstruck won her the Oscar

Mark Wahlberg
54
Marky Mark to Boogie Nights to The Departed

Jared Leto
54
30 Seconds to Mars frontman, Oscar winner

Jennifer Lopez
56
Selena, Out of Sight, Hustlers

Queen Latifah
56
Chicago, Hairspray, The Equalizer
Will Smith slapped presenter Chris Rock on stage at the 2022 Oscars, then went on to win Best Actor for King Richard later that night.
Lady Gaga's Joker: Folie a Deux bombed at the box office in 2024, earning Razzie nominations three years after House of Gucci launched a second Oscar campaign.
Jennifer Lopez's snub from the Hustlers Oscar race became one of the most-discussed cases of the Academy overlooking crossover stars.
Queen Latifah turned her acting career into a CBS franchise with The Equalizer, which drew over nine million viewers and ranked as one of the network's strongest scripted performers.
Jared Leto played WeWork founder Adam Neumann in WeCrashed (2022), a pivot after the critically panned Morbius.