While watching Harry Edward Styles maniacally shimmy and shake on the big screen during Don’t Worry Darling, I couldn’t help but wonder to myself, “How did we get here?” It was nearly impossible for me to reconcile my conception of Styles as one of the most famous pop stars in the world with the character he was trying to portray on screen. So in honor of Harry Styles’ foray into acting (My Policeman and Don’t Worry Darling premiered in 2022 and he had guest roles in Eternals and Dunkirk), I thought I would compile a list of musicians who succeeded (and failed) in the film industry.

Bing Crosby

As the first multimedia superstar, Bing Crosby forged an entirely original and immensely successful career path. While crafting hit songs and propelling the “crooner” style to worldwide renown, Crosby signed with Paramount Pictures and began starring in movie musicals. His “White Christmas” rendition still holds the Guinness World Record for best-selling single for Christmas with over 100 million copies sold. He subsequently starred in the film White Christmas which became the highest-grossing musical at the time of its release in 1954. Crosby is one of 33 people to have three stars on the Hollywood walk of fame and also garnered an Academy Award and a Grammy Lifetime Achievement Award for his work.

Barbra Streisand

Barbra Streisand sang in nightclubs in New York City before making her Broadway debut at the age of 19. After receiving rave reviews for her work, she signed a record deal with Columbia Records and released her first album, The Barbra Streisand Album. It won two Grammy awards and peaked at number nine on the Billboard 200. She continued pursuing a music career with other successful albums and Broadway productions such as an acclaimed turn as Fanny Brice in Funny Girl. She reprised this iconic role for her first blockbuster film of the same name and won the Academy Award for Best Actress for her performance. Streisand remains one of few in Hollywood to win an Emmy, a Grammy, an Oscar and an (honorary) Tony.

Jennifer Hudson

In 2004, Jennifer Hudson debuted on the third season of "American Idol" and made it to the top seven before her untimely elimination. Unlike the other entries on this list, Hudson’s incredible vocals earned her an acting role in Dreamgirls before she ever debuted an album. She won an Oscar for her show-stopping performance and in 2009, she won a Grammy for her first album Jennifer Hudson. Hudson has also won an Emmy, a Grammy, an Oscar and a Tony award, becoming the second African American woman to earn EGOT status.

Lady Gaga

After dropping out of the New York University Tisch School of the Arts to pursue a music career, Lady Gaga became a fixture of New York City’s underground electropop scene before scoring multiple record deals. Her record-smashing debut album The Fame won two Grammys and a rerelease titled The Fame Monster won three. Gaga remains the first and only female artist to sell over 10 million copies of four separate songs. After three more incredibly successful albums and several acclaimed television acting gigs, Gaga achieved movie stardom with her leading role in the 2018 remake of A Star is Born. With her hit song “Shallow,” Gaga became the first woman to win an Academy Award, a BAFTA, a Golden Globe Award and a Grammy within one year. But, while attempting to play a murderess in House of Gucci, Gaga’s fictional husband wasn’t the only one to fall victim to a hit. Even after speaking in an Italian accent for nine months, a House of Gucci dialect coach called her accent more Russian than Italian. Both casual viewers and critics alike found her campy performance enjoyable but too hammy. Yet the role did not murder her acting career as she is set to star as Harley Quinn in the Joker sequel, Joker: Folie à Deux.

Harry Styles

Does Harry Styles deserve to be on this list? Probably not, or at the very least, not yet. While Styles has achieved pop superstar status with several chart-topping albums and singles, the success of his acting endeavors remains to be seen. He’s had more roles than Lady Gaga, but his most recent leading man endeavors in Don’t Worry Darling and My Policeman”received lukewarm reviews at best.

This list is filled with cultural icons who shattered records and pioneered new paths for creative expression. While some of their projects have been less rewarding, they continue to push boundaries. Styles owes his opportunities to these trailblazers and hopefully, he will live up to the incredible legacy they have and continue to create as musicians-turned-actors.

Thumbnail image "Harry Styles - Xcel Energy Center, 9/22/2021" by Erin Mc is licensed under CC BY 2.0.