Photo: Mgm/Kobal

Whether or not Lady Gaga walks away with Best Actress this year, she has already joined a rarified company. Not musicians who have dabbled in the movies — cinema is littered with those, from Madonna to Ludacris to KISS Meets the Phantom of the Park. Still, only a couple dozen of them have managed to garner the Academy’s respect, elevated to the stratosphere of, quote, unquote, “serious” actors, rather than mere dilettantes or [haughty, drawn-out sniff] pop stars.

What differentiates a musician’s Oscar-worthy performance from a regular one? As with all things Oscars, much of it surely comes down to timing, and the inscrutable confluence of events that collectively determines the movies and performances to be singled out each year. Lord knows it’s not singing or dancing, otherwise Elvis would have cleaned up. But look at the list of those who have made the leap and a pattern emerges. Many of the best acting turns from musicians build on some element of their persona, often subverting the audience’s expectations of who they are based on what they’ve shown onstage. Sometimes it means just stripping away the layers of costuming and choreography to find the vulnerable, recognizably human being underneath. Sometimes it’s about going even bigger, in a way that maybe more cautious, more “serious” actors wouldn’t dare. In each and every case, however, it’s something that prompts us to say, “I didn’t know they could do that.”

In attempting to rank all 25 of the Oscar-nominated turns from musicians before Gaga’s big night, we largely focused on that element of surprise, asking what their performance did or didn’t reveal about the depths of their talents. (It’s an admittedly subjective and possibly illogical process — just like the Oscars themselves.) And for the many musicians who didn’t make the Academy’s cut to find themselves on this list, well, they can always fall back on their day job.

25. Bobby Darin, Captain Newman, M.D. (1963)

Nominee: Best Supporting Actor

Though he died at age 37, the eclectic pop star and songwriter Bobby Darin had an eventful 17-year career in showbiz, during which he recorded everything from teenybopper novelty tunes like “Splish Splash” to sophisticated crooner fare like “Beyond the Sea” to hip folk-rock like “If I Were a Carpenter.” He chased trends, savvily — including joining the wave of singers like Frank Sinatra who were trying to stretch themselves by making serious movies. Darin’s only a small part of Captain Newman, M.D., a World War II drama about a U.S. Army psychiatric facility. But the film itself is surprisingly progressive in its sensitivity toward soldiers suffering from PTSD. Darin gives a vanity-free performance — to the point of overacting at times — playing a cocky flyboy who has trouble admitting his feelings of guilt and anxiety.

24. Doris Day, Pillow Talk (1959)

﻿Nominee: Best Actress

A successful interior decorator, Jan (Doris Day) is forced to share a telephone line with her neighbor, a womanizing theater composer named Brad (Rock Hudson). After seeing her dance one night, he decides that he wants her, but because of their previous fights over the phone line, must pretend he’s someone else for her to return any feelings. Pillow Talk may feel like any number of romantic comedies based on a case of mistaken identity, but its adorable stars share so much onscreen chemistry, it’s still a thrill to watch. As Hudson puts on one of his most charming performances of his career, Day matches his energy with an outwardly confident presence and a lively inner monologue that reveals her fears and doubts about a new paramour. Day’s singing skills are never central to the plot and feel like more of an afterthought, but that gives her plenty of screen time to dig into one of the most persistent fears experienced by women of that era: Were their careers getting in the way of love and marriage?

23. Maurice Chevalier, The Big Pond (1930)

Nominee: Best Actor

The same year that Maurice Chevalier was nominated for Best Actor for The Love Parade (covered above), he competed against himself. In The Big Pond, the French singer and bon vivant plays a good-hearted working-class schmo who falls in love with a swell, played by Claudette Colbert. Like a lot of movie stars in the first half of the 20th century, Chevalier’s screen persona didn’t vary much from role to role. The major movie studios typed him as a lighthearted romantic, perpetually gleeful that he got to live in a world populated by so many pretty women. Still, it’s no mean feat to be so effortlessly charming. Although he lost the Oscar to George Arliss (in one of his two nominated parts that year, playing a famed British prime minister in Disraeli), Chevalier’s introduction to Hollywood established a performing style that would remain popular for decades.

22. Mark Wahlberg, The Departed (2006)

Nominee: Best Supporting Actor

Looking back, it’s hard to say what distinguishes Mark Wahlberg’s performance in The Departed from a career spent playing Boston-baked tough guys. (Although, similar sentiments could be expressed for the film’s Best Picture and Best Director wins.) Wahlberg was by then long removed from his swaggering “Marky Mark” days, of course, and he’d arguably turned in more revelatory roles in films like Boogie Nights, Three Kings, and even Rock Star by the time he signed on to play a foulmouthed, yet principled, police sergeant in Scorsese’s knotty gangster drama. Nevertheless, Wahlberg earned his first Oscar nod for Best Supporting Actor by tapping into those old hothead, hometown-boy origins, which are sublimated here into a series of hostile, witty, fahk-ing harangues he sprays in all directions. Wahlberg reliably steamrolls over everyone from Leonardo DiCaprio to Alec Baldwin to Martin Sheen, while the script charitably gives him all its best lines, so perhaps it’s easy to see why the Academy would have singled him out for the film’s sole acting nomination. Still, entertaining as it is, there’s been more interesting work from him both before and since.

21. Queen Latifah, Chicago (2002)

Nominee: Best Supporting Actress

The first verse of Queen Latifah’s Grammy-winning 1993 single “U.N.I.T.Y.” could have been nicked right from the litany of confessions filling out the middle of Chicago’s signature showstopper “Cell Block Tango”: “I walked past these dudes when they passed me / one of them felt my booty, he was nasty /…/ Huh, I punched him dead in his eye / and said, ‘Who you calling a bitch?’” He had it coming, right? Latifah’s take-no-shit attitude toward triflin’-ass men made her a perfect fit for Cook County Prison’s palm-greasing Mama Morton, who sees the inmates in her charge less as hysterical murderesses than people reacting rationally to sleazeball behavior, and primarily as sources of mutually beneficial profit. Sure, she’s a living manifestation of the “hire more women guards” tweet, but what she lacks in feminist virtue she more than makes up for with sheer va-va-voom in her big number “When You’re Good to Mama.” With a lustrous finger-waved do, an ostrich-feather fan, and an industrially reinforced bustier, she invites Josephine Baker to eat her heart out.

20. Maurice Chevalier, The Love Parade (1929)

﻿Nominee: Best Actor

The conventional wisdom about Hollywood’s transition to the sound era is that directors suddenly locked their cameras down and abandoned the expressionism of the silent cinema. Apparently nobody sent that particular memo to Ernst Lubitsch. His first sound film — the sophisticated musical comedy The Love Parade — is visually splendid, with smooth camera moves, clever editing, and opulent sets and costumes. What really catches the eye though are Lubitsch’s stars: Jeanette MacDonald as a young European queen being pressured into a respectable marriage, and Maurice Chevalier as the roguish diplomat she tries to tame. Though he was already a wildly popular recording artist, Chevalier had limited range as a singer. But he could do a lot with his eyes, and his smile. In The Love Parade, Lubitsch watches him closely, as he plays a carefree gent who’s never met a woman he couldn’t bed.

19. Bing Crosby, The Country Girl (1954)

﻿Nominee: Best Actor

Side by side with Bob Hope, Bing Crosby was one of Paramount Pictures’ biggest stars in the 1940s, entertaining millions with his pleasantly foggy singing voice and affectless hepcat patter. But the public’s tastes began changing in the ’50s, and Hollywood’s old guard did its best to keep up, making serious movies dealing with social issues and featuring more darkly shaded characters. That’s how Crosby ended up showing a much different side of himself in writer-director George Seaton’s adaptation of Clifford Odets’s play The Country Girl. Playing a former theatrical star turned embittered alcoholic — who spends his days sniping at his long-suffering wife, played by an Oscar-winning Grace Kelly — Crosby lets loose his insecurities, petty jealousies, and deepest regrets. It’s not the easiest film to watch, given that some of the actor’s real-life children have described him as a privately cold and often abusive father. But it does feel bracingly honest.

18. Bette Midler, For the Boys (1991)

﻿Nominee: Best Actress

Bette Midler was at her big-screen best in The Rose (see below), but the musical dramedy For the Boys may be her most complete movie role. Once again directed by The Rose’s Mark Rydell, she plays Dixie, another popular performer, singing songs to huge crowds — in this case the U.S. troops in World War II, Korea, and Vietnam. Dixie’s act in For the Boys is more like Midler’s actual show, mixing genuine sentiment with raunchy jokes. The performance is full of life and wit, and plays well off of James Caan’s turn as Eddie, Dixie’s fast-talking co-star and occasional lover. The actress lost the Oscar to Silence of the Lambs’ Jodie Foster, who gave a performance that’s proved more enduring. But it’s too bad this film flopped, because American cinema in the ’90s could’ve used another half-dozen Midler pictures where she sings like an angel and swears like a sailor.

17. Burl Ives, The Big Country (1958)

﻿Winner: Best Supporting Actor

With his sweetly raspy voice and wizened air — both cultivated during long years on the road as a troubadour — Burl Ives developed a reputation in the mid-20th-century as one of the world’s great folklorists, even though he was more a self-taught expert than an actual academic. Ives carried that casual worldliness to Hollywood, proving equally credible as a southern aristocrat, a buffoonishly grumpy naval captain, or a cruel New England farmer. The sweeping Western The Big Country was one of the many 1950s movies that tried to elevate the genre by putting it into a more realistic historical and psychological context. As a struggling-but-stubborn Texas rancher who’s a thorn in the side of his more prosperous and ambitious colleagues, Ives fits right into this more mature filmmaking. He comes across like a character in one of his own songs: a complicated common man, fighting to hold on to what he’s built.

16. Barbra Streisand, The Way We Were (1973)

﻿Nominee: Best Actress

Although Barbra Streisand hasn’t made that many movies during her long, multifaceted career, it’s still surprising that The Way We Were contains just her second and (so far) last Oscar-nominated performance. It’s a gusty one, too. Streisand’s Katie Morosky is a fiery leftist Jew, who’s at once a sparring partner, lover, and nagging voice of conscience to the reserved Wasp writer Hubbell Gardiner, played by Robert Redford. The film spans decades in their relationship; and throughout, the actress often pushes past the boundaries of “likability,” for the sake of the picture’s theme. The Way We Were is a film that divides even staunch Streisand fans, with some finding her too abrasive — and blaming Redford and director Sydney Pollack for boxing her into such a broad take. But others find this one of the truest romantic melodramas ever made, understanding that sometimes differences in personalities and values are just too hard to bridge.

15. Ann-Margret, Tommy (1975)

﻿Nominee: Best Actress

The mild frumpiness Ann-Margret had to endure for her previous Oscar-nominated turn in Carnal Knowledge was nothing compared to what she went through on Tommy, where the pop star was forced to slither around in a muck of baked beans, detergent, and chocolate for three days with a lacerated hand. Ken Russell’s phantasmagoric reading of the Who’s rock opera doesn’t seem like a natural Oscar contender, particularly in a year when the socially conscious realism of Dog Day Afternoon and One Flew Over the Cuckoo’s Nest reigned. But it garnered a nomination anyway for her performance as the eponymous pinball wizard’s mom, with Ann-Margret gamely matching Russell’s excesses as her character goes from pitiable to sleazy and borderline psychotic over the span of 20 years. Like Tommy itself, it’s a performance that wavers on the line separating psychedelic and just plain silly, but you can’t say Ann-Margret doesn’t give it everything she has. Let’s see Louise Fletcher writhe around in slop and maintain her dignity.

14. Peggy Lee, Pete Kelly’s Blues (1955)

﻿Nominee: Best Supporting Actress

By 1955, when she took a plum supporting role as woebegone jazz singer Rose Hopkins in this fitfully melancholic musical, Peggy Lee had worked her way through two of four marriages that would all end with acrimonious divorce. Lee knew all too well how unreliable, disappointing, frustrating, and cruel men could be, and she channeled that terrible knowledge into her performance as a woman at the mercy of those who claim to love her. Hopkins appears on the scene as the arm candy of gangster Fran McCarg (Edmond O’Brien), having been gifted like a caged songbird by him as a gesture of goodwill to the speakeasy in which the film takes place. She dulls the pain of her glorified servitude with booze, but the combination of alcohol, despair, and a clearly disinterested crowd leaves her silent. After McCarg’s taken out all of his embarrassment on her in violently abusive fashion, both Hopkins and Lee linger as twin images of perseverance: heartbroken, hurt, but alive.

13. Frank Sinatra, The Man With the Golden Arm (1955)

﻿Nominee: Best Actor

After From Here to Eternity proved he could do more than croon and chase dames, Sinatra earned his second acting nomination by playing a junkie jazz drummer in Otto Preminger’s The Man With the Golden Arm. In an adaptation of Nelson Algren’s novel, Sinatra plays Frankie Machine, a sympathetic hoodlum in the Marlon Brando mold. (In fact, Sinatra had snaked the role away from Brando, partly as revenge for losing the lead in On the Waterfront.) Newly sober and fresh out of jail, Frankie tries to avoid falling back in with his old gang and bad habits while chasing his musical dreams, but he inevitably succumbs to his addictions while a parade of gangster-melodrama archetypes slowly put the screws to him. The movie earned the ire of the Production Code Administration for daring to depict drug abuse, meaning it handles the subject with all the nuance of an educational filmstrip. But Sinatra’s performance remains (relatively) naturalistic, with the king of swingin’ cool coming off as a convincingly empathetic underdog, even when he’s in the twitchy, flop-sweat stages of withdrawal. Sinatra eventually lost the statue to Ernest Borgnine and Marty, but Man With the Golden Arm confirmed that Sinatra deserved to be taken seriously as an actor.

12. Dexter Gordon, Round Midnight (1986)

﻿Nominee: Best Actor

Saxophonist Dexter Gordon earned a Best Actor nod for his role as a hardscrabble jazz musician in Bertrand Tavernier’s elegy for the bebop generation, one of just a handful of acting gigs Gordon took on toward the end of his career. While his character, Dale Turner, was explicitly inspired by other jazz greats who found their way to Paris in the late ’50s, like Bud Powell and Lester Young, Gordon — a fellow former expat — more or less plays himself, imbuing Turner’s struggles to scratch out a living and stay upright with authentic experience, along with a palpable regret. Gordon’s voice — a weary, raspy murmur that picks its way carefully through the largely improvised dialogue — has the same slow-and-low sadness as the notes he coaxes from his sax, while his moments with a French fan turned patron (Francis Borler) build from Gordon’s legendarily warm stage presence. There’s not much “acting” going on here, particularly since Tavernier avoids the boulevard-of-broken-dreams melodrama typical to stories like these. It’s so subtle and subdued, he stood little chance against Paul Newman’s far flashier turn in The Color of Money. Nevertheless, like jazz, it still feels like an authentically soulful expression, where the big notes are rarely the main point.

11. Cher, Silkwood (1983)

﻿Nominee: Best Supporting Actress

As Cher has often recalled, when her name first appeared in the Silkwood trailer, alongside Meryl Streep and Kurt Russell, audiences laughed. The singer had earned raves for her performance in Robert Altman’s Come Back to the 5 & Dime, Jimmy Dean, Jimmy Dean, but to most people she was still Cher, the wisecracking, bell-bottomed glamour-puss of The Sonny & Cher Comedy Hour. She was hardly the obvious choice to play the scrappy lesbian friend of real-life nuclear whistleblower Karen Silkwood, or star alongside Meryl Streep in a timely, serious drama. But after she stripped away every last vestige of her Cher-ness — reportedly even submitting to director Mike Nichols’s daily spot-checks to ensure that she wasn’t sneaking makeup — she was left only with the self-assurance and strength that was always at its core. In the process, she earned her first Oscar nod. Merely holding her own against her co-stars would have been enough, but Cher elevated what could have been a stock character, even at a time when LGBTQ roles often fell back on easy stereotypes. From then on, no one was laughing.

10. Will Smith, The Pursuit of Happyness (2006)

﻿Nominee: Best Actor

The two times Will Smith has been nominated for a Best Actor Oscar, he’s had the ill fortune of going up against showier, more scenery-chewing performances. No offense intended to the always formidable Forest Whitaker’s work as Idi Amin in the offbeat drama The Last King of Scotland, but in 2006 he wasn’t anywhere near as great as Smith is in The Pursuit of Happyness. Based on the memoir of Chris Gardner — a man who risked everything to become a successful stockbroker, while handling homelessness and single parenthood — The Pursuit of Happyness could’ve been just a sappy rags-to-riches story. Instead, Smith and director Gabriele Muccino keep the movie grounded in the practical realities of Gardner’s life, focusing on his insistence on maintaining dignity and excellence, even while living in poverty. This is a feel-good film that doubles as an astute social critique, detailing the lengths that even a highly capable person has to go to make it when he or she doesn’t have money or connections.

9. Bing Crosby, Going My Way (1944) / The Bells of St. Mary’s (1945)

﻿Winner: Best Actor / Nominee: Best Actor

Though they were released a year apart and each tell their own distinct stories, Going My Way and The Bells of St. Mary’s feature one extended performance by Bing Crosby, under the direction of Leo McCarey. The pop singer plays Father Chuck O’Malley, a hip young Catholic priest with a knack for connecting to young people, and for reviving struggling parishes. In the first film, he helps an older priest (played by an Oscar-winning Barry Fitzgerald) understand that he needs to be more open-minded. In the second, he butts heads with a similarly stubborn nun (played by an Oscar-nominated Ingrid Bergman). Father O’Malley is one of the rare movie roles that genuinely deserves to be called “iconic,” given that Crosby’s take on the crooning, compassionate pastor would become a model not just for other pretend padres, but for the nonfictional ones as well.

8. Jennifer Hudson, Dreamgirls (2006)

﻿Winner: Best Supporting Actress

The film adaptation of the musical Dreamgirls cast Beyoncé in a Diana Ross–inspired part, but by the time the credits rolled, it was clear that this was Jennifer Hudson’s movie. As the eventually discarded member of the movie’s namesake girl group, Effie White (Hudson) struggles against the gears of the ruthless music industry. In a way, the movie can be distilled into one showstopping moment, when abandoned by her friends, brother, and lover, White belts out the “And I’m Telling You I’m Not Going” number to an almost empty room, a show of strength with flashes of vulnerability behind every note. It’s just her voice and her emotions, alone in the spotlight. Hudson showed off an impressive vocal range and acting chops in her movie debut, and it would earn her the Oscar for Best Supporting Actress.

7. Bette Midler, The Rose (1979)

﻿Nominee: Best Actress

Thanks to her frequent Tonight Show guest appearances and her bawdy retro cabaret act — honed in New York’s gay bathhouses — Bette Midler was already a star before she signed on to play a self-destructive rock goddess in The Rose, a lightly fictionalized version of Janis Joplin’s life story. But few people who’d seen her bubbly, winking stage shows could’ve expected her to give such a raw performance as Mary Rose Foster, a lusty belter seemingly always teetering between raucous laughter and heavy sobs. This kind of persona — and this kind of music — wasn’t really what Midler was known for in the ’70s. But as somebody who’d thrived during one of the music business’s most dangerous, druggy eras, the actress likely didn’t have to reach too far down to tap into the bruised defiance of a woman who’d been exploited, overlooked, and condescended to through her whole hit-making career.

6. Ann-Margret, Carnal Knowledge (1971)

﻿Nominee: Best Supporting Actress

Ann-Margret was dubbed the “female Elvis” early in her singing career, a comparison reinforced when she starred opposite Elvis himself in Viva Las Vegas. To some extent, her role as Bobbie in Mike Nichols’s Carnal Knowledge is the sort of stock deglamorizing that the Oscars love to reward. She gained weight and stifled her famous, hip-shaking vivaciousness to play a lust object who lapses into depression once it becomes clear that Jack Nicholson’s self-loathing sleaze has no other use for her. But there’s something deeper beneath Bobbie’s surface that Ann-Margaret taps into, often glimpsed just behind her eyes. As she would discuss in interviews, it’s a wounded resolve that connects implicitly to a career similarly marred by exploitation and abuse. The result is a performance that similarly unearthed a complexity beneath the camp, with Ann-Margret garnering the film’s sole Oscar nomination, then going on to the kind of respected acting career that films like Kitten With a Whip had never even hinted at.

5. Will Smith, Ali (2001)

﻿Nominee: Best Actor

Because Muhammad Ali had such a distinctive vocal cadence and way of carrying himself, it might’ve been simple for Will Smith to coast through director Michael Mann’s biopic doing a mere impression. Instead, Smith smartly and sensitively separates the public and private Ali, capturing both the blustering braggadocio that made the boxer an international celebrity, and the quiet humanity that made him a hero. Ali takes place during the ten most tumultuous years of its subject’s life, during which he became heavyweight champion, converted to Islam, refused to serve in Vietnam, and made a stirring comeback after being banned from the sport. There’s a remarkable physicality to Smith’s performance, which covers the champ’s spry youth and his more lumbering middle age. But the reason he deserved to win Best Actor that year (even over Training Day’s Denzel Washington, who was admittedly overdue) is the way he captures Ali’s mind, always thinking his way through the righteousness of any given situation, and not always coming to the easiest conclusion.

4. Diana Ross, Lady Sings the Blues (1972)

﻿Nominee: Best Actress

Diana Ross hands over her mind, body, and soul to play Billie Holiday in the film based on the pioneering singer’s autobiography. Lady Sings the Blues opens with Holiday’s 1945 arrest, showing Ross with disheveled hair, tear-stained face, and bellowing guttural screams. Ross did not take on this project for the glamour, but for the challenge. By the scene’s end, she is lying on the floor in a straitjacket, restrained but not empty. It will not be the only time Ross sacrifices her presence to embody Holiday’s struggles. Ross plays Holiday as an artist who swings wildly from overconfident and belligerent to shy and vulnerable, especially in scenes opposite Billy Dee Williams, a singer who tries to get her to clean up her act. The movie plows through many of Holiday’s personal tragedies, like rape, separation from her mother, poverty, discrimination, and drug addiction, but it’s Ross’s performance that humanizes the artist’s struggles beyond the tabloid headlines.

3. Cher, Moonstruck (1987)

﻿Winner: Best Actress

The Best Actress category for 1987 was a tough one, one that included the enduring work of both Holly Hunter in Broadcast News and Glenn Close in Fatal Attraction. Still, credit is due to Cher, whose turn in Moonstruck gives Norman Jewison’s loopy comedy its emotional center, helping it stay grounded even as a feral Nicolas Cage — as the brooding, wooden-handed “wolf” who tries stealing her heart from his brother — does everything but growl and bite random passersby. Cher had already proven herself a nimble actor in both comedy and drama by this point, but Moonstruck was the first to combine those qualities into one complex, fully rounded character that — while still far removed from her flashy, Bob Mackie world — felt like a natural extension of the persona she’d been developing since she first started giving Sonny Bono shit. She also delivers the most memorable slap in cinema history, and neither Hunter nor Close can lay claim to that.

2. Frank Sinatra, From Here to Eternity (1953)

﻿Winner: Best Supporting Actor

He doesn’t get to play tonsil hockey with Deborah Kerr in the cascading surf, but Sinatra gets all the best lines in this ravishing tragedy playing out during the lead-up to Pearl Harbor. Every regiment has a black sheep, and on Oahu, that’s Sinatra as Private Angelo Maggio. Right off the bat, he messes with the wrong guy by smashing the bejesus out of Fatso Judson (Ernest Borgnine) after the sadist gets a little too friendly with a picture of Maggio’s sister. Some inebriated impropriety lands him in the stockades under Fatso’s jurisdiction later on, where the grim prison life gradually grinds all the humanity out of the poor bastard. When a harried, brutalized Maggio escapes just in time to die in his totally platonic best friend’s arms, he’s barely recognizable as himself — not just as the former, fast-living Maggio, but as the Sinatra who had grown synonymous with debonair, effortless charm. The Academy loves a celebrity willing to play against type, and Sinatra wowed audiences with his range.

1. Barbra Streisand, Funny Girl (1968)

﻿Winner: Best Actress

Barbra Streisand was practically born to play vaudeville-era comedian and singer Fanny Brice, given that both were New Yorkers who endured the ups and downs of showbiz thanks to prodigious talent and indomitable will. Streisand first took on the role in the 1964 Broadway musical Funny Girl, which became a valedictory moment in her young career, arriving a few years after she battled to the top of the pop-music charts. But she failed to win a Tony, losing to Carol Channing in Hello, Dolly! (in a part Streisand, in a sublime act of revenge, would play on film five years later). So there’s perhaps an extra sense of purpose to her performance in the movie Funny Girl, which showcases her wry sense of humor and her subtly naturalistic way of expressing heartbreak … as well as her powerhouse voice on the showstopper songs “People” and “Don’t Rain on My Parade.”