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Best Album: FutureSex/LoveSounds (2006)
Best Role: The Social Network (2010)
No one doubts JT is an across-the-board performer who delivers in whatever genre he picks up. He's the complete package, and his turn in David Fincher's Facebook movie benefited from his irrepressible swagger. But it's Timberlake's music career that's garnered him the most accolades, and his 2006 collaboration with Timbaland (itself a master class in R&B-infused pop) still stands as the apex of Timberlake's artistry. Individual songs from FutureSex/LoveSounds won two Grammys, and the visually seductive video for ''What Goes Around Comes Around'' merged both JT's interests in what might be five of music's finest minutes. All that and he brought sexy back, y'all.
2 of 20
Best Album: Like a Prayer (1989)
Best Role: Evita (1996)
The gospel-infused Like a Prayer spawned six singles, topped the charts, and led to the infamously controversial music video for the title track, cementing Madonna's status as an international pop force. And say what you will about her acting work, but her turn as Eva Peron in Evita nabbed her a Golden Globe for Best Actress, and the film landed an Oscar for Best Original Song. All that said, the Material Girl's always been at her best when the material is a touch divisive. The Pope may not have appreciated it at the time, but Her Madgesty's Prayer answered all ours.
Winner: Like a Prayer
3 of 20
Best Album: Big Willie Style (1997)
Best Role: The Pursuit of Happyness (2006)
One of the more diverse artists out there, Smith offered us a chance to get ''Jiggy Wit It'' and take a little trip to ''Miami'' with his album, then the chance to stir our souls with his movie. The former got him two Grammy wins, and the latter snagged him an Oscar nod (his second, after 2001's boxing biopic Ali). It pains us to choose because Willie's hooks are so darn infectious, but they don't quite have the same texture as Happyness — a film that, ironically, is perfect when you need to get your sad on. It's all about balance, and Smith's career has been exemplary in that regard.
Winner: The Pursuit of Happyness
4 of 20
Best Album: Jennifer Hudson (2008)
Best Role: Dreamgirls (2006)
The former American Idol contestant's self-titled debut album snagged her a Grammy win for Best R&B Album. Dreamgirls proved she is not only a power belter but a strong actress. The Academy agreed, awarding her the Oscar for Best Supporting Actress. Both projects were telling us she wasn't going anywhere. But you! And you! And you! Well?you know which is really best.
5 of 20
Best Album: Live Like You Were Dying (2004)
Best Role: Friday Night Lights (2004)
The lyrical decadence of ''I went 2.7 seconds on a bull named Fu Manchu'' on the titular track of McGraw's Live Like You Were Dying is definitely?moving. But watching the beloved, generally be-hatted country singer take a turn toward the dark side as Garrett Hedlund's abusive FNL father had an eye-opening pop with which McGraw's eighth album just can't compete. And the balding mullet — oh, the balding mullet!
Winner: Friday Night Lights
6 of 20
Best Album: Doggstyle (1993)
Best Role: Starsky & Hutch (2004)
When ABC's Starsky and Hutch debuted in 1975, Calvin Broadus (a.k.a. Snoop Dogg-turned-Lion) was only 4 years old, yet he was clearly born to play the role of underworld boss Huggy Bear. Luckily for him, they made a movie version 29 years later, and Snoop's birthright was fulfilled. Snoop's true calling, however, was to be the coolest SoCal rapper of all time, and his Dr. Dre-produced debut was the perfect introduction — not to mention the perfect soundtrack for sippin' that iconic '90s cocktail: ''Gin and Juice.''
7 of 20
Best Album: Dangerously in Love (2003)
Best Role: Dreamgirls (2006)
As great as Dreamgirls was as a whole, there's almost nothing that can top the album that gave us Beyoncé and Jay-Z's collaboration on ''Crazy in Love'' — and that's not even mentioning ''Baby Boy'' or ''Me, Myself and I.'' Jennifer Hudson might have won an Oscar for Dreamgirls, but Bey's best work remains in the recording studio.
Winner: Dangerously in Love
8 of 20
Best Album: The Predator (1992)
Best Role: Boyz n the Hood (1991)
Cube channeled much of the socioeconomic frustration of inner-city life in Predator, which was released within months of the '92 Los Angeles race riots. Much of the album's angst (as exemplified by the signature track ''It Was A Good Day'') was also expressed in his portrayal of Doughboy in John Singleton's drama. Hood remains Cube's best dramatic work (with 1995 cult comedy Friday standing up as his best comedy and ushering him to a new act as film producer and mainstream success), but the brilliance of his work as a musician in Predator really gets the heart of what put Cube on the map in the first place.
Winner: The Predator
9 of 20
Best Album: Live Through This (1994)
Best Role: The People vs. Larry Flynt (1996)
With Hole's breakout album, Courtney Love proved to be much more than just Kurt Cobain's wife; she was a grunge goddess in her own right. The album landed on multiple best-of lists in '94 and established Love as a cultural icon. Then she went and reinvented herself as a critically acclaimed actress in the Hustler founder's biopic, earning a Golden Globe nomination along the way. So which is the real Love? Well, we prefer the rock widow with too much eyeliner, just the right amount of peroxide, and a cigarette dangling from her lips, so...
Winner: Live Through This
10 of 20
Best Album: Music for the People (1991)
Best Role: The Fighter (2010)
Music for the People gave us two things we can be thankful for: ''Good Vibrations'' and the name ''Marky Mark and the Funky Bunch.'' But Wahlberg's portrayal of real-life boxer Micky Ward in David O. Russell's The Fighter knocks out its musical competition, no matter how catchy the songs.
Winner: The Fighter
11 of 20
Best Album: Daydream (1995)
Best Role: Precious (2009)
If we can just forget Glitter ever existed (which we've all been doing for more than a decade now), Mimi has had a pretty stellar big-screen career, thanks to her work with director Lee Daniels (Precious, The Butler). But let's be honest: She could be nominated for more Oscars than Meryl Streep and still never top the magic of her 1995 album, which spawned three No. 1 hits: ''Always Be My Baby,'' ''Fantasy,'' and the best-selling single of the '90s, the Boyz II Men collaboration ''One Sweet Day.''
12 of 20
Best Album: Like Water for Chocolate (2000)
Best Role: Hell on Wheels (2011-present)
Chicago rapper Common was part of a movement that was sometimes derisively called ''backpack rap'' (back then, he was known as Common Sense). His first few albums are the trail mix of rap music, but Like Water for Chocolate manages to balance his brainy positive vibes with more pop-friendly grooves thanks to production by Roots drummer Ahmir ''?uestlove'' Thompson. It's a tough, groovy album with a deep debt to the horrors of history — exactly like his performance on Hell on Wheels. His work on AMC's underrated railroad Western has been solid, but Chocolate is too rich to ignore.
Winner: Like Water for Chocolate
13 of 20
Best Album: Cher (1987)
Best Role: Moonstruck (1987)
Cher had a truly massive '87: In November of that year, she released her self-titled comeback album that sounds like a tribute to '80s excess (Michael Bolton, Jon Bon Jovi, Bonnie Tyler, and Diane Warren all pitched in) but actually carries off the bombast thanks to Cher's undeniable musical charisma (the top 10 Bolton-penned hit ''I Found Someone'' is especially sticky). A month after the release of Cher, she opened Moonstruck, as charming and smart a romantic comedy as has been made. Though she was making a triumphant return to music after a five-year hiatus (you know, like Justin Timberlake), Moonstruck ended up being the bigger triumph, as it earned Cher an Oscar for Best Actress.
14 of 20
LL Cool J
Best Album: Mama Said Knock You Out (1990)
Best Role: NCIS: LA (2009- )
LL Cool J established himself again as a hip-hop force with Mama Said Knock You Out — though, as the title track commands, ''Don't call it a comeback/I've been here for years.'' The artist's acting career follows the same mantra, having played Special Agent Sam Hanna for years on the NCIS spin-off that consistently attracts strong ratings. While he's displayed consistency on CBS, we prefer his unpredictable rhythms on FM overall.
Winner: Mama Said Knock You Out
15 of 20
Best Album: J.Lo (2001)
Best Role: Out of Sight (1998)
It's true that ''Love Don't Cost a Thing'' could be considered J.Lo's greatest contribution to music (and music videos), but no matter how ''real'' she might be, we can't overlook her chemistry with George Clooney in Out of Sight. Call us crazy, but we prefer her with a badge as opposed to a bathing suit.
Winner: Out of Sight
16 of 20
Best Album: Back for the First Time (2000)
Best Role: Crash (2004)
Ludacris created quite a roar with his loud, boisterous debut Back for the First Time with hits such as ''What's Your Fantasy'' and ''Southern Hospitality.'' He broke out as an actor with similar vigor as a carjacker in Paul Haggis' Oscar-winning tapestry Crash. Though Luda racked up awards for his part in that ensemble, his solo work has always been a better showcase for his talent.
Winner: Back for the First Time
17 of 20
Best Album: Coverage (2003)
Best Role: Saved! (2004)
She was mostly known as an also-ran during the boom of bubblegum pop stars in the late '90s, breaking out with her singles ''Candy'' and ''I Wanna Be With You.'' But it was her fourth studio album, Coverage, that attempted to establish her as a real artist with depth. While critically praised, the album failed to sell well. During the early aughts, Moore had more luck with movies, first as scene-stealing mean girl Lana in The Princess Diaries and then starring in teen favorite dramedy A Walk To Remember. But it was her role as hypocritical teenage evangelist Hilary Faye in the cult dark comedy Saved! that won her the most support — and additional roles.
18 of 20
Best Album: O.G. Original Gangster (1991)
Best Role: Law & Order: SVU (2000-present)
As good as Detective Odafin ''Fin'' Tutuola's no-nonsense one-liners are on SVU, the role — like the procedural formula that spawned it — has become a bit one-note over time. Look back a few decades, and Ice's seminal album O.G. Original Gangster was breaking ground for early '90s West Coast rap, flawlessly infusing his provocative lyrics with heavy metal twists. This T is better when he's mixing it up.
Winner: O.G. Original Gangster
19 of 20
Best Album: Mos Def & Talib Kweli Are Black Star (1998)
Best Role: Something the Lord Made (2004)
Before he changed his name to Yasiin Bey and starred in flicks like the quirky Be Kind Rewind, Mos Def was one of the best rappers around at the turn of the century. His solo debut Black on Both Sides is a funky blast of street soul, but his finest work came on Mos Def & Talib Kweli Are Black Star, a tag-team effort with friend Kweli. Over dense, soulful beats, Def and Kweli brought philosophical underground hip-hop to the mainstream and remains one of hip-hop's greatest turn-of-the-century statements. Def peaked relatively early as an actor, too: In portraying Vivien Thomas, a groundbreaking black cardiologist, in the exquisite 2004 HBO flick Something the Lord Made, Mos earned himself nominations for Best Actor in a Television Movie or Mini-Series at both the Emmys and Golden Globes. He's turned his attention to acting in recent years, and we can see why.
Winner: Something the Lord Made
20 of 20
Best Album: Black Reign (1993)
Best Role: Chicago (2002)
Before she was a Covergirl or a crooner, Latifah was one of the illest lady rappers in the game, and hits like ''U.N.I.T.Y.'' made Reign her most successful outing in music, opening doors for her acting career. Though a steady gig on Fox's Living Single raised her profile, her Oscar-nominated turn as saucy cellblock sister Matron Mama Morton rocketed her into the stratosphere, opening another chapter in her career that eventually led her back to her roots in vocal performance with jazz standard album The Dana Owens Album. Reign may have proclaimed her royalty, but Chicago was her true coronation.