20. Elvis Presley
The King of Rock and Roll's movie career is both the archetype and warning for every single performer on this list. "Love Me Tender," Presley's first of 33 films, made him a even bigger star than he was when it was released in 1956. But through the 1960s, the singer -- more specifically his manager Colonel Tom Parker -- favored quantity over quality, releasing a slew of critically panned films that watered down his once unshakeable sound. The worldwide celebrity continued yet the results were now unpredictable.
19. Janet Jackson
A perennial television star in the 1970s and '80s -- remember Willis' girlfriend Charlene from "Diff'rent Strokes?" -- Jackson made the transition to film in 1993 in John Singleton's "Poetic Justice," a romantic road trip film featuring Tupac Shakur. Singleton's follow-up to "Boyz n the Hood" was a surprise hit, though Jackson chose to focus primarily on her music through the next decade. She's since tried her hand at comedy as Eddie Murphy's girlfriend in "Nutty Professor II: The Klumps" and has recently turned up in a few Tyler Perry productions ("Why Did I Get Married?", "For Colored Girls").
18. Mandy Moore
If you are a teenage girl, you can probably recite Mandy Moore's lengthy filmography by heart; if not, just know that the pop star starred in 18 movies between 2000 and last year, including the lead role in Disney's 2010 Rapunzel update "Tangled." While Moore's films have been more strikeouts than hits, she excels in films like "Saved!," the 2004 satire on fundamentalist Christianity that upended her stereotypical Goody Two Shoes image.
17. Tupac Shakur
Tupac may be remembered as the embodiment of bravado and machismo, but his vulnerable, artistic talents were on display well before any of the rapper's headline-grabbing antics. Shakur's training as a student of Baltimore School for the Arts prepared him well for films like "Juice," "Poetic Justice" and "Above the Rim." With every role, Shakur's intensity dominated the scene, with the 1,000-yard stare of his eyes conveying more than most full scripts. If Tupac focused all his energy on acting, he could've been one of the greats.
16. Ice Cube
Arguably the most successful rapper/actor and indisputably the most successful Ice-themed rapper/actor, O'Shea Jackson has gone from politically charged, incendiary emcee to building a mini-empire as an actor, screenwriter, producer and director. As Doughboy in John Singleton's classic urban drama "Boyz n the Hood," the rapper pulled off both the intimidating and heartfelt sides of his character. He would subsequently build up a wide roster of films, including drama ("Higher Learning"), action ("Anaconda") and, who would have guessed?, comedy, with the "Friday," "Barbershop" and "Are We There Yet?" franchises all successful enough to spark multiple sequels.
15. Dolly Parton
The Queen of Country will always be known as one of the genre's preeminent and prolific singers and songwriters (more than 40 albums and counting), but when it comes to film, it's quality over quantity. Parton's first two roles, 1980's "Nine to Five" and 1982's "The Best Little Whorehouse in Texas" both garnered her Best Actress Golden Globe nominations, while her role in "Rhinestone" actually made Sylvester Stallone sound slightly more comprehensible. More recently, the singer can be heard in the animated feature "Gnomeo and Juliet."
When her life was tragically cut short at the age of 22 in 2001, R&B singer Aaliyah Haughton was robbed of more than just a singing career. As Trish O'Day in the 2000 martial arts film "Romeo Must Die," the singer displayed an acting range well beyond her years. The success of "Romeo" led to the 2001 vampire film "Queen of the Damned," where the singer played Queen Akasha. While the film was panned, the singer was once again singled out for her acting ability. Upon her death, she was scheduled to star as Zee in The Matrix Reloaded, a role that eventually went to Nona Gaye, the daughter of legendary soul singer Marvin.
13. David Bowie
Nicolas Roeg's "The Man Who Fell to Earth," the story of an alien sent to Earth to retrieve the planet's water only to fall in love with the foreign land, couldn't have been more perfect for David Bowie's first starring role. An innovative musician who routinely incorporated theater, performance and character into his work, Bowie always seemed more alien (in both senses) than any of his peers. Whether as a vampire in "The Hunger," Andy Warhol in "Basquiat" or Jareth the Goblin King in "Labyrinth," Bowie's singular talents and unique view of the world ensure that a "standard" Bowie performance will never exist. And we wouldn't have it any other way.
12. Mos Def
The lyrical, thought-provoking emcee has always had a gift for performance, so it's no surprise Mighty Mos got his acting start at 14 in a made-for-TV movie. In addition to numerous theater and television appearances -- that's him as Dante Beze in the short-lived "The Cosby Mysteries" -- the rapper has primarily opted for lower-profile, yet artistically significant works including "Monster's Ball" and "The Woodsman." More recently, he starred with Jack Black in Michel Gondry's flawed but creative "Be Kind Rewind" and played Chuck Berry in the more flawed but less creative "Cadillac Records."
11. Dean Martin
With Frank Sinatra, part-time actor/full-time singer/fuller-time drinker Dean Martin led The Brat Pack, a group of entertainers in the 1960s who all appeared in each other's films and albums. Martin dominated nearly every entertainment field for more than a decade, and while he never won the awards, his film career spans nearly 40 years and includes a series of Westerns, war films and the classic caper film "Ocean's Eleven." We're partial though to 1968's "5 Card Stud," the first Western-noir ever produced.
10. Courtney Love
The Hole frontwoman should be on this list for every time she gave Oscar-winning performances of sobriety and normalcy (rimshot!). Before Hole even existed, Love could be seen in Alex Cox's "Sid and Nancy," -- insert joke here --the acclaimed biopic on Sid Vicious and his girlfriend Nancy Spungen. A decade later, despite massive studio misgivings, Love was cast as Althea Flynt, wife of hustler magnate Larry Flynt, in 1996's "The People Vs. Larry Flynt," earning a Golden Globe nomination for Best Actress and a Golden Cup for passing every drug test. Shocking nearly everyone, Love would repeat the unanimous acclaim in "Flynt" three years later alongside Jim Carrey in "Man on the Moon."
9. Queen Latifah
After the release of her third album "Black Reign" in 1993, Queen Latifah began her acting career in earnest as one of a group of African-Americans living in Brooklyn on the popular FOX show "Living Single. " The 1990s would bring the "U.N.I.T.Y." rapper minor roles, but it was her portrayal of Matron "Mama" Morton in Rob Marshall's "Chicago" that brought the Queen into a new level of royalty and earned her an Academy Award nomination for Best Supporting Actress. Her acting career has had spotty results since ("Taxi"? Really?), but in her comfort zone, as in the 2007 musical "Hairspray," Her Highness still reigns.
8. Jennifer Hudson
Few singers have had as much acting success from their debut performance as former "American Idol" contestant Jennifer Hudson. As the hot-blooded Effie White, member of the Supremes-styled Dreamettes, Hudson played opposite, and upstaged, Beyoncé and Eddie Murphy, taking over the film with her booming voice and towering presence. She went on to win the Academy Award for Best Supporting Actress and followed up "Dreamgirls" with a supporting role in "Sex and the City" and a lead role in "The Secret Life of Bees."
7. Bing Crosby
The most popular performer of the 1930s and '40s, actor and singer Bing Crosby, along with frequent partner Bob Hope, made some of the most enduring films in history and became the first American pop star to successfully forge a career in film. While Crosby and Hope's "Road" series, a set of seven films combining adventure, humor and musical interludes and taking place in remote parts of the world, became the actor's most notable legacy, the "White Christmas" crooner picked up a Best Actor Academy Award for 1944's "Going My Way" and two Best Actor nominations for the film's sequel "The Bells of St. Mary's" and 1955's "The Country Girl."
6. Justin Timberlake
"Yogi Bear" and "The Love Guru" notwithstanding, the former 'N Sync megastar has done a 180 from his squeaky clean upbringing when it comes to film, choosing dark, grimy roles in films such as "Alpha Dog" and "Southland Tales." While the singer added to his comedy roster with this summer's comedies "Bad Teacher" and "Friends With Benefits," it was 2010's performance as Napster co-founder and Facebook mentor Sean Parker that silenced any remaining JT naysayers.
5. Barbara Streisand
Love her or hate her, they don't come much bigger than Babs, a multi-talented singer, actress, filmmaker and producer whose cinematic reign starts with an Best Actress Academy Award for 1968's "Funny Girl" and extends to this day with the "Fockers" series. In between, she remains one of the few entertainers who has picked up Oscar nominations or wins for Best Picture (1991's "The Prince of Tides," which she directed), Best Song (1976's "A Star is Born") and Best Actress (along with "Funny Girl," Streisand earned a nomination for 1973's "The Way We Were.") So basically Hall of Fame in every category you can envision.
4. Frank Sinatra
The conventional wisdom about the Chairman of the Board is that his hubris at being "Frank Sinatra" overshadowed the necessity to, well, act in movies. But when he found the right roles -- see his harrowing, Oscar-nominated portrayal as a drug addict in "The Man With The Golden Arm" and the rough Captain Marco in the spy thriller "The Manchurian Candidate" -- no one could do confident better. Arguably his most well-known role, though, is the 1953 wartime classic "From Here to Eternity," a role that earned the actor his only Academy Award for Best Supporting Actor.
3. Mark Wahlberg
Make all the Marky Mark jokes you want. Who would've thought in 2011, the erstwhile rapper and Funkiest of Bunches would be an A-list actor with an Academy Award nomination to his credit (Best Supporting Actor for Martin Scorsese's "The Departed"). Films like "The Substitute" and "Fear" are hardly the auspicious start any actor hopes for, but as local loser-turned-porn star Dirk Diggler in Paul Thomas Anderson's "Boogie Nights," Wahlberg received universal acclaim and went on to expand his résumé into comedy ("I Heart Huckabees," "The Other Guys"), drama ("Three Kings") and action ("The Perfect Storm"). Wahlberg's reign continues to this day, with his subtle portrayal of Micky Ward in "The Fighter" earning the actor his first Best Actor nomination at the Golden Globes.
If the only thing you know about the cinematic side of Cher is the recent flop "Burlesque," you have about 30 years of catching up to do. The singer/actress/variety show staple received a Best Supporting Actress Golden Globe nomination for 1982's "Come Back to the Five and Dime, Jimmy Dean, Jimmy Dean," one of her earliest roles. "Silkwood" would win her the same award a year later, while 1987's romantic comedy "Moonstruck" with Nicolas Cage earned her a Best Actress Oscar (a rarity for a comedy). We'll always be partial, though, to her tough-but-loving Rusty Dennis, the mother of Rocky Dennis in "Mask." We may act tough, but that last scene gets us every time.
1. Will Smith
In the late 1980s to mid-1990s, Will Smith helped usher in the post-Biz Markie lighter, playful side of hip-hop, both with family-friendly tracks ("Parents Just Don't Understand," "I Think I Can Beat Mike Tyson") and his massively successful TV show "The Fresh Prince of Bel-Air." Beginning in 1993, however, Smith showed that hip-hop's consummate goofball had a serious, dramatic side, with his searing portrayal of a young con artist in "Six Degrees of Separation." Leading roles in "Bad Boys" and "Independence Day" would follow, and Smith quickly found himself as one of the most bankable stars in Hollywood. Fifteen years later, he has yet to relinquish the throne. While Jazzy Jeff was busy getting thrown out of houses, Smith picked up Best Actor Academy Award nominations for his portrayal of boxer Muhammad Ali in "Ali" and in 2006's" The Pursuit of Happyness."
Originally published Feb. 10, 2011.