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Will Smith Elvis Presley Madonna

Written by Matthew Pejkovic

With the news that pop starlet Rihanna will make her debut in Battleship, it is time to step back and look at the best and worst “singers” turned actors. 





Will Smith

“Big Willy” Will Smith may be the biggest star in Hollywood, but his career began as a teenage hip hop star The Fresh Price, spitting rhymes with DJ Jazzy Jeff, being the first recipient of the first ever Grammy for Best Rap Performance.

TV stardom came next in the popular sitcom The Fresh Prince of Bel-Air, before making a splash on the big screen in 1993 with Made in America and Six Degrees of Separation, the latter turning heads with his performance as a homosexual con artist.

Since then Smith has succeeded in the comedy, action, drama, and sci-fi movies, making over a billion dollars at the box office in the process. 

Movie Career Highlights
Oscar nominations for Ali (2001) and The Pursuit of Happyness (2006). Cornering the action market with turns in Bad Boys (1995), Independence Day (1996), and Men in Black (1997).



Mark Wahlberg

Formerly known as Marky Mark, this bad boy from Boston led his Funky Bunch to a number #1 hit record with the song “Good Vibrations”.

It would not take long for his music career to plummet due to controversy and lack of interest, and a new avenue was found in acting, with Wahlberg making his career debut in Penny Marhsall’s Renaissance Man (1994).

Strong turns in The Basketball Diaries (alongside Leonardo DiCaprio) and Fear (1996) followed, before breaking through as porn star Dirk Diggler in Paul Thomas Anderson’s Boogie Nighs (1997).

A mixed bag of performances followed, with mostly exceptional work, especially in the action/crime genres.

Movie Career Highlights
Receiving an Oscar nomination for his work in Martin Scorsese’s The Departed (2006). Giving strong support in The Basketball Diaries (1995) and I Heart Huckabees (2004), while proving his leading man credentials in Boogie Nights and Three Kings.




From her double act with Sonny Bono, to straddling a Navy war carrier in her knickers with “If I Could Turn Back Time”, turn the synthesized botox pop of recent years, the ever changing Cher has made an undelible mark in the music industry.

Equally successful too was Cher the movie star, where in her fourth feature she earned her first Oscar nomination for her supporting turn in Silkwood (1983). A strong turn in Mask (1985) would follow, and then an Oscar win as best lead actress in Moonstruck (1987).

Cher is set to make a movie comeback in the musical Burlesque, where she will co-star alongside younger fozes Christina Aguilera and Kristen Bell. Will she still have that big screen charm?

Movie Career Highlights
Stealing the show in Robert Altman’s Come Back to the Five & Dime, Jimmy Dean, Jimmy Dean (1982), followed by strong turns in Silkwood (1983) and Mask (1985). A 1987 triple threat with Suspect (alongside Dennis Quaid), The Witches of Eastwick (standing toe to toe with Jack Nicholson), and Oscar gold with Moonstruck.



Frank Sinatra

The Chairman of the Board was as impressive in front of the lens as he was behind the microphone, exuding a natural ability on screen that many of his peers could not match.

Musicals, of course, were his first foray into the movie biz, with turns in Anchors Aweigh (1945) and On the Town (1949) highlights. Yet it would be his comeback supporting turn in From Here to Eternity (1953) that would secure his place as an actor to be respected, winning the Best Supporting Actor as the doomed Pvt. Angelo.

The ‘50s and ‘60s saw even more fine work from Sinatra, with The Man with the Golden Arm (1955) and The Manchurian Candidate (1962) highlights. 

Movie Career Highlights
Strutting his stuff in the musicals On the Town (1949) & Guys & Dolls (1955), showing off his dramatic chops in The Man with the Golden Arm (1955) and The Manchurian Candidate (1962), winning the Oscar for From Here to Eternity (1953).



Mos Def

While his hip-hop career is not as prominent outside of the US, his performances in films as varied as The Italian Job (2003) and Be Kind Rewind (2008) brought wider exposure.

Indeed it was Mos Def’s turn as the neighbour to Billy Bob Thornton’s redeemed racist in Monsters Ball (2001) which made many stand up and take notice, with even more prominent performances in the likes of The Woodsmen (2004), Something the Lord Made (2004), and 16 Blocks (2006).

Also standing out is his sketch work in The Dave Chappelle show, where he displayed an ability to do comedy and do it well.

Movie Career Highlights
Putting Billy Bob in his place in Monster’s Ball (2001), haunting Kevin Bacon’s paedophile in The Woodsmen (2004), and strutting his stuff as Chuck Berry in Cadillac Records (2008).




Vanilla Ice

The one hit wonder known as Vanilla Ice (real name Robert Matthew Van Winkle) tried his hand at acting with the Rebel Without a Cause rip off Cool As Ice (1991), where he played a bad boy rapper who saves a conservative town from itself.

The film was a commercial and critical failure, and banged the final nail in Vanilla Ice’s career. Future movies included the Matrix spoof The Helix...Reloaded (2005) , and the hip hop western Big Money Rustlas (2010) alongside fellow douche bags the Insane Clown Posse.




Queen of pop she may be, yet Madonna’s success as pop phenom did not transfer to the big screen. While Desperately Seeking Susan (1985) showed some spark, it didn’t take long for it to fizzle with Shanghai Surprise (1986), where Madonna acted alongside her then beau Sean Penn to devastating results.

Somehow she managed to snag roles in Dick Tracy (directed by then boyfriend Warren Beatty) and A League of Their Own (1992), before her dismal turns in the erotic thriller Body of Evidence (1993) and Swept Away (directed by then husband Guy Ritchie. See a connection?) declared her dead weight in the acting game.

A Golden Globe win for her turn in Evita (1996) still stands as one of the biggest upsets in the Award shows' history.    



Elvis Presley

The King of Rock ‘n’ Roll was a dud on screen, starring in a succession of formula pics which were really package deals to sell his latest hit song.

Presley played a variety of roles ranging from assassin (Harrum Scarrum), race car driver (Spinout), and cowboy (Charro!) yet displayed no range while doing so. Many point the finger of blame to Presley’s overbearing manage Col Tom Parker, who –amongst over things – forbade Presley from excepting a role in West Side Story (1961).

Regardless, the evidence on hand may show a gifted entertainer, but not much of an actor.  



Jessica Simpson

If your biggest cinematic accomplishment is strutting in a pink bikini for the slack jawed masses, then acting is not your strongest suit.

Proving that tits do indeed make this woman, Jessica Simpson’s turn as Daisy Duke in The Dukes of Hazzard (all 4 mins of it) was nothing more than eye candy in place of talent.

Follow up performances in Blonde Ambition (raking in a poor $1190 on its opening night) and the straight to DVD Major Movie Star (2008) did not make for stimulating nor entertaining viewing.



Snoop Dogg

It is probably due to the weed, but could Snoop Dog at least put a little effort into his acting? Even when playing flamboyant snitch Huggy Bear in Starksy & Hutch (2004), the west cop rapper couldn’t raise a pulse with his dreary delivery. His attempt at becoming a hip hop horror king are not any better, with Bones (2001) and Hood of Horror (2006) straight to DVD stinkers.


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