20 Celebs Who Have The Chops To Win An Oscar And A Grammy

It's come to this, the age-old question of which is more impressive, an actor who can sing or a singer who can act? Or, which is harder, being able to sing or act at a high, award-winning level? Obviously, no one other than actors or musicians care about these questions but as fans, it's still fun for us to find out that someone who is already rich and famous in one form of entertainment can double that money and fame thanks to being talented in another form of entertainment.

All jokes aside, it truly is cool to see a favourite actor randomly release an album that doesn't suck or perform in a musical and catch us off guard with their voice. On the flip side, it's always a treat to see a musician pop up in a movie or TV show and hold their own, either with a powerful performance or by showing their comedic timing.

Everyone on this list has succeeded in crossing over to either the acting or singing side and accomplish it in different ways. They don't have to win a Grammy or an Oscar to prove they were successful (although that does help). There are some who jumped ship for good and are better off for it, others who just dabbled on the other side before returning to their home and even some who continue to play both sides and excel at both. So, here they are - 10 Actors Who Showed They Can Sing and 10 Singers Who Showed They Can Act!

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20 Chris Pine Is Underrated In More Ways Than One


Even though Chris Pine has branched out from popcorn flicks like Star Trek and gave powerful performances in Oscar nominated movies like Hell Or High Water, it feels like he doesn't get the recognition he deserves as an actor. So it should come as no surprise that his singing abilities get zero recognition too because Captain Kirk can flat out sing! This was on full display in the movie Into The Woods where he held his own vocally with the stacked cast, most notably Meryl Streep.

His co-star Anna Kendrick even praised his singing and described it as being "crooning and smooth."

That wasn't his first foray into singing on screen, though, but it was definitely seen by way more people than his first attempt a couple years back. Pine can be seen in the straight-to-DVD movie Small Town Saturday Night as an aspiring country music star, where he performs on stage and wins over the crowd in a bar as well as the audience watching at home, or more accurately, the clip on YouTube. If his singing performances in those movies didn't convince people of his talent, then maybe the fact that Barbara Streisand asked him to do a duet with her on her album Encore: Partners Sing Broadway just might.

19 Will Smith Raps and Acts


It's been so long since Will Smith released an album that it's easy to forget he got his start in music as the Fresh Prince. It also doesn't help that the show that jumpstarted his acting career went by the same name. Regardless, Smith was a musician before taking on acting full time, and he was good at it, too, considering he won the first-ever Grammy for Best Rap Performance in 1989 (whether or not he deserved it though is a different discussion). As an actor, Smith didn't have the instant success that he did in music, as he had to climb every rung on the ladder to get where he is today.

Smith was able to build his acting career more and more after every role and go from TV star to supporting actor in movies, followed by leading roles in blockbusters that made him a movie star and finally Oscar-nominated roles that led him to superstardom.

Sure, his acting career exceeded the heights of his music career by miles but his roots are in music and he owes his early success in life to it. Plus, some of his movies are best remembered for the songs he wrote for them.

18 Amy Adams Only Sings In Movies


Early on in her career, Amy Adams was known for her supporting work and even nabbed an Oscar nomination for Junebug but when she finally got a starring role in Enchanted, she not only showed that she can be a leading lady and a box-office draw, but that she is a double threat who can sing!  Since then, she's gone on to build a successful acting career and received four more Oscar nominations but she doesn't shy away from a musical role from time to time and it's always a treat when she does.

Her singing doesn't go unrecognized either as two of the songs she sang in Enchanted were nominated for Best Original Song at the Oscars and she performed "Happy Working Song" during the show.

She even branched out to the theatre and played the Baker's Wife in Into The Woods a year before the film was released. With her career taking off, her last singing role was in The Muppets movie, but there is an Enchanted sequel in the works called Disenchanted and considering she said no one will play Giselle but her, she'll more than likely be in it. Her music career is only contained to acting roles though as she claimed in an interview for Enchanted that she has zero interest in making an album.

17 Mark Wahlberg Ditches The Funky Bunch


It's been a while since Mark Wahlberg was associated with music but no one will ever forget that one of the most intimidating people in Hollywood got his start as the rapper Marky Mark who had a crew called the Funky Bunch. His music career started off promising too, as his debut album went platinum, however, subsequent ones never came close to replicating that success and his career immediately took a nosedive. He wisely got out before it was completely ruined and tried to salvage it by transitioning to acting. Obviously, he would reach new heights as an actor but his success was far from a surefire thing. Things got off to a promising start with a star-making turn in Boogie Nights, but subsequent flops would put his talent into question. Unlike his music career, Wahlberg was able to bounce back and even though it's been a roller coaster ride he's seemed to have found his footing and remains at the top.

An Oscar-nominated performance in The Departed showed he has the potential to be great and comedic turns in Ted and The Other Guys showed off his range.

He clearly made the right career move by becoming an actor, however, if he ever did decide to bring the Funk Bunch out of retirement, people probably wouldn't be too upset.

16 Zooey Deschanel Starts A Band


Zooey Deschanel enjoyed minor success early on in her career and even got to share the screen with comedy legends like Will Ferrell and Jim Carrey as their love interest in Elf and Yes, Man respectively. It wasn't until landing two leading roles, one for the anti rom-com (500) Days of Summer and the other for the hit TV show New Girl did her career start to take off. Coincidentally, both roles feature Deschanel singing in some capacity, which may have come as a surprise to most fans at first but in retrospect makes perfect sense as one of her strengths as a performer is singing.

She is far from just an actress who only sings in movies though, as she is a legitimate singer/songwriter and one half of the band She & Him, which has released six studio albums to date.

She was even asked to write the theme song for New Girl, which ended up being used and performed by her. She isn't shy about her singing either, which is evident in New Girl as her character is constantly bursting out in song, or on YouTube where she can be seen singing alongside (500) Days of Summer co-star Joseph Gordon-Levitt. She is adorable for a reason.

15 Who Knew Ice Cube Was Funny?


Ice Cube has one of the best transitions from rapper to actor and not in terms of accomplishments but by the hilarious notion that he went from a gangster rapper performing the song about the police to playing a police captain in 21 Jump Street. Anyway, Cube made it big as part of the rap group NWA before going solo and establishing himself as one of the best rappers in the game.

It wouldn't be long until Cube made the jump to movies and was perfectly cast in Boyz n the Hood where he was praised for his performance and showed he could possibly make a run at this acting thing.

Since then, he's appeared in a variety of films, from comedy to action, and even wrote a few himself, but he has yet to replicate that first performance. However, he realized his strength lies in comedy and has gone on to give scene-stealing performances, most notably in the Jump Street movies. Sure, Cube is never going to win an Oscar, but he knows what he's good at and sticks to those roles. Plus, his recent single "Good Cop, Bad Cop" showed he hasn't lost his music touch, which is something not everyone on this list can say.

14 Of Course Ryan Gosling Can Sing


There is no denying Ryan Gosling's acting ability, as he shines again and again in every film he makes. It wasn't until La La Land though, that he proved he is a man of many talents by acting, singing, dancing and even playing the piano at such a high level that John Legend was impressed. The piano playing may have stood out more above the rest, but there was no doubt that Gosling could hold his own in the singing department, which had been teased but never fully realized throughout his career. When he was a kid and a member of The Mickey Mouse Club, he sang from time to time but was generally overshadowed by his co-star and future NSYNC member Justin Timberlake. Gosling finally sang on the big screen in Blue Valentine, but it was short and he started off singing in "a goofy voice" before going with his more natural sound and leaving people wanting more, which they ended up getting in La La Land.

What many people may not know, though, is that singing isn't some gimmick to him as he takes it seriously outside of movies. He's also a member of the band Dead Man's Bones. They've only released one album, back in 2009, but one of their songs was featured in the movie The Conjuring.

If anyone didn't know Gosling was in that band it's probably because he performed under the alias Baby Goose for some reason.

13 Cher Is A Master Of All


Cher juggled singing and acting when she did The Sonny and Cher Comedy Hour with her Sonny Bono, her husband at the time, but her music career came first and foremost as she found success as a duo and even more as a singles act throughout the '60s and '70s. It wasn't until the '80s when she decided to fully commit to acting in feature films, and just like music, she instantly showed she was a natural. In only her second film, Silkwood, she was nominated for an Oscar, and then a few years later took one home for her performance in Moonstruck.

After Moonstruck, she essentially left acting and returned to music. She's appeared in a few minor roles here and there, mostly in cameos. Honestly, she proved she could conquer the acting world like she did the music world so her going back to her roots made sense. With that being said, she seems to have caught the acting bug once again, or maybe she just wants to show anyone who may have forgotten that she is still one of the best in the game. She'll be returning to acting in Mama Mia! Here We Go Again, where she'll be going toe-to-toe with Meryl Streep one more time.

12 Jamie Foxx Trades Laughs For Applause


Jamie Foxx built a career on being funny as he found success early on as a stand-up comedian before transitioning to sketch comedy when he landed a role on the TV show In Living Color. He would then make the jump to feature films and take a stab at dramatic roles, where he quickly found success and ended up winning an Oscar for his portrayal of Ray Charles in the biopic Ray. His acting obviously blew everyone away but it was his singing that really stuck with people and opened the door for him to switch up his career once again.

Foxx's music career can be summed up as before Ray and after Ray. Some people may not know this about Foxx but he dropped an R&B album in 1994 right when his career was starting to take off. It was positively received but he didn't seem to be taken seriously as a musician and was somewhat seen as just another actor who thinks he can sing, until Ray. Foxx seemed to want to prove he could have a career in music and he arguably did thanks to multiple Grammy-award nominations and finally a win. It wouldn't be completely out of the question either to say that some people may even prefer Foxx the singer over Foxx the actor.

11 Jennifer Hudson Doesn't Stay Down For Long


Jennifer Hudson first popped up on everyone's radar when she appeared on American Idol. She was a fan favourite and a top contender to win but ended up being eliminated at number seven. Her departure was met with some controversy as viewers saw her as the strongest contestant on the show hands down. Being unceremoniously dumped must have lit a fire under her though, as she went on to give award-winning performances right out of the gate, in both music and acting. She is considered a singer first and foremost but post American Idol she wasted no time in displaying her acting chops, too.

She quickly landed a role in Dreamgirls and even though it was a musical that played to her strengths, it was her acting that blew everyone away and she was rewarded for it.

She holds the honor of being one of the few actors to win an Oscar in their feature film debut as she took home the award for Best Supporting Actress. To cap that off, she went back to the studio and recorded her debut album that went on to win Best R&B album at the Grammys. Music is clearly her passion but she continues to dabble in acting from time to time and usually when she does she takes on musical roles and gives us the best of both worlds.

10 Donald Glover Is A Genius


Donald Glover has proven again and again that he is one of the most talented entertainers of his generation and a genuine Jack-of-all-trades. There doesn't seem to be any form of entertainment that he hasn't tested his skills in and not only does he end up succeeding at it, he's great at it. It's been fun watching his career grow throughout the years from writer to actor to stand up comedian and finally creator and star of his own TV show. However, his music career is just as impressive, as he's been able to flawlessly transition his style from rapper to R&B artist. Is there a step or two above triple threat? Because that's where Glover is.

His first two albums were fine, but it was his last one, Awaken, My Love! that grabbed everyone's attention and earned him his first Grammy win. People were so impressed with his vocals on the album, specifically the song "Redbone," that they began speculating that vocal effects were added to his voice.

Glover and his co-producer on the album, Ludwig Goransson, insisted that nothing was added, with Glover stating, "there was no vocal pitching on the album — I just sang differently" and Goransson adding, "we didn't pitch his voice; that's all him singing." Finally, to shut everyone up for good, Glover performed "Redbone" live on Jimmy Fallon and blew everyone away.

9 Eminem Is One and Done


Eminem has accomplished nearly everything in the music world that one can as he's won numerous Grammy Awards, his albums have gone multi-platinum and he truly is a rap god. There isn't much else to say, as even people who aren't fans of rap know and listen to Eminem. However, his foray into acting was much different as he basically gave it a shot once and hasn't really gone back since.

Not including an uncredited cameo in The Wash, Eminem has only appeared on screen four times, and three of those times he was playing himself, with the one exception being his feature film debut in 8 Miles. What's so impressive about the movie is that in his first attempt at acting he was the star and was in every single scene. Sure, it was semi-autobiographical and was filled with a lot of rap battles, but he still delivered a raw and passionate performance that left people wanting more. And he could have given it to them, as he was offered leading roles in Elysium, Jumper, and Southpaw, but turned them all down. Eminem's movie career, aside from a few cameos, may forever only be 8 Mile, but at the end of the day, that's not a bad resume for something like him to have and it won him an Oscar for Best Original Song, which ties it up nicely.

8 Anne Hathaway Sings Her Way To An Oscar


Anne Hathaway hasn't been too picky when it comes to film choices throughout her career as she has acted in nearly every genre. However, when it comes to her singing career, it involves one constant: Hugh Jackman. Maybe it's because she can only sing when he's in the room, kind of like how some people can only sing in the shower. Anyway, Hathaway gave glimpses of her singing skills a few times at the beginning of her career, first in the movie Ella Enchanted, which was fine but didn't really leave people wanting more.  That changed after two strong, albeit comedic performances at the Oscars, both times involving Jackman.

The 2009 Oscars saw Hathaway do a duet with Jackman, and even though she talked more than she sang, it was impressive nonetheless. Then at the 2011 show, she parodied the song, "On My Own" from Les Misérables, joking that Jackman refused to perform with her this time.

She displayed much more range and it's even speculated that this performance was an unofficial audition for Les Misérables, which she ended up getting a part in. She knocked it out of the park as her acting and singing skills were in full force, and her rendition of "I Dreamed A Dream" left people in tears. It was solidified when she won the Oscar for Best Supporting Actress.

7 David Bowie Does A Lot With A Little


With a career that spanned 50 years, it feels like words cannot describe David Bowie as he was in a league of his own in terms of talent and how often he changed his style and persona. He burst onto the scene with the song "Space Oddity" in 1969 and would go on to have a successful pop career before transitioning to rock and reaching new heights. Near the tail end of the '70s, he would take a chance at acting but bounced in and out of it for years and never seemed to give it a true shot.

The few roles he did take on he was enjoyable to watch and added some of his Bowie charm to the movie. His acting career can be summed up with a fine performance in the cult classic Labyrinth and a great surprise cameo in Zoolander.

Perhaps the closest look into what Bowie could have accomplished as an actor, though, came in his small part in The Prestige where he played Nikola Tesla. Even in Labyrinth, he always seemed to just be playing a version of himself but here he fully embraced being Tesla. He never did follow up on that performance but he gave enough to show he belongs in the discussion of singers who can act. Plus, come on, it's David freaking Bowie.

6 Emma Stone Sings Her Way To Our Hearts


Emma Stone has been slowly but surely winning over our hearts throughout her career with standout performances that span multiple genres. She was able to make the jump seamlessly from supporting actress to leading lady and hasn't looked back since. Then, she shocked and impressed moviegoers and critics when she acted, danced and sang her way to an Oscar in La La Land.

She established herself as a triple threat, but anyone who was surprised to hear Stone sing for real in the movie hasn't been paying close enough attention to her career.

Easy A gave Stone an opportunity to carry a movie and she succeeded at that, but not many know she also gave a quick look at her other talents, as she sang for real in the movie. The performance didn't scream "Grammy Award," but it showed she could deliver much more if given the opportunity. Even though she admitted she hates hearing herself sing, that didn't stop her from acting in the Broadway production of Cabaret, which ended up being somewhat of an audition for La La Land. Damien Chazelle, the director of the movie, caught one of her shows and loved her performance. Stone didn't know he was going to be there and admitted she was sick during the show. Clearly, it didn't have much of an effect on her performance.

5 Queen Latifah Conquers Both Worlds


Queen Latifah got into music at a young age, singing in choirs and even in the bathroom and locker rooms of her high school. She started a female rap group and then garnered the attention of a producer with her solo work that led to her releasing a single at 18 and a full album the following year. Throughout her music career, she would go on to earn seven Grammy nominations and collect one win for her song "U.N.I.T.Y.," but it wasn't long after her career started taking off that she decided to test the waters in acting. She quickly nabbed a role in the TV show Living Single, which she was fine in, but the show was mainly praised for being groundbreaking at the time by having a predominately black female cast.

She would juggle both music and acting for a while and appeared in various genres until 2002 when she landed a role in the movie Chicago.

This role would finally earn her recognition for her acting skills and lead to her winning the Oscar for Best Supporting Actress. She hasn't repeated that success since but she has given award worthy performances in smaller films throughout her career, which have proven she is worthy of the label of actor.

4 Robert Pattinson Should Open Up More

It feels like Robert Pattinson has been trying to climb his way out of the gigantic money hole he dug himself when he took on the lead role in the Twilight franchise. He's had a hard time being taken seriously as an actor for a while now but has slowly been rebuilding his career with risky roles in David Cronenberg movies and, more recently, the critically-acclaimed Good Time. However, Pattinson would have never disappeared completely if acting never worked out as his backup plan has always been to pursue a career in music.

He likes to keep his hidden talent, well, hidden, as he has said he doesn't plan on putting out an album unless acting doesn't work out, which is a shame because he is quite the talented singer and songwriter.

It's possible only Twilight fans are aware of this but he actually had two of his songs featured on the soundtrack and also had a few on the soundtrack for the movie How To Be. It seems like the only thing holding him back from a music career is himself as he's said, "I'm always playing and recording but I don't know. People hate when actors become musicians so I've been avoiding it for the longest possible [time]." Regardless, everyone should do themselves the favor and check out his music.

3 Barbra Streisand...That Says It All


To label Barbra Streisand as merely a singer who showed she could act seems like a disservice to her career and a massive understatement. Streisand excelled at everything she did, and even though there's an asterisk beside her EGOT status (someone who has won an Emmy, Grammy, Oscar and Tony Award) in the Tony category, she's been nominated twice for a Tony so that's proof enough. When we break it down though, she was clearly better at one area than the other and considering she is the "highest-selling female recording artist of all time," it should go without saying which one it is.

She's been more prominent in the music industry with a career that spans 50 years, but when it comes to her acting career, she won an Oscar right out of the gate, stuck around for a bit, got nominated again, and then sort of left on a high note for a few years.

She returned in Meet The Fockers and Little Fockers and even though she is funny in them, they're nothing compared to her performances at the beginning of her career. Regardless, the movies she's done in the last 10 to 15 years don't matter as much as she proved years ago that she's a superstar.

2 Anna Kendrick Has Perfect Pitch


After bit parts in movies, Anna Kendrick showcased her full potential with an Oscar-nominated performance for her supporting role in the movie Up In The Air, and then proved she was a star with a leading role in the box-office hit Pitch Perfect. This was also the movie that showed off her voice as she sang in it, a lot. Since then, she's gone on to star in two more Pitch Perfect movies to complete the trilogy and even found time to play Cinderella in the musical Into The Woods. Add to that the fact that her song "Cups" from Pitch Perfect got radio play and a music video separate from the movie and there's no denying Kendrick is equally talented on the mic as she is on film. However, anyone who has been following Kendrick's career since she was a kid, which would be kind of weird unless they were a kid too, but anyway,

they would know that Kendrick got her start on Broadway and was the second youngest actress ever to be nominated for a Tony award.

On top of that, her first feature film was the indie musical Camp, so it's only fitting her career went full circle and she got her big break in a movie about a college a cappella group.

1 Live From New York, It's Justin Timberlake!


It was obvious from the get-go that Justin Timberlake was the stand out in the boy band NSYNC and he ended up being the only one to find any success after the group split. He forged a tremendous solo career in which he reinvented his sound on more than one occasion and has won numerous awards for his music. He seemed to be content with a music career but then began popping up in movies here and there and it was always a surprising treat when he did. Timberlake had experience acting at a young age as part of the Mick Mouse Club, but it was a silly kids show where acting wasn't the top priority.

Jump ahead a few years and he gets a role acting in the indie movie Alpha Dog and steals every scene he's in, then goes on to earn high praise for his role as co-founder of Napster Sean Parker in The Social Network.

He then showed his comedy side in movies Bad Teacher and Friends With Benefits, but where Timberlake truly stood out as an actor was with his Saturday Night Live hosting gigs, where he took home a few Emmys for his performances. It's interesting to wonder if he had gone the acting route right away like his Mouseketeer buddy Ryan Gosling if he would have found as much success as he did as a musician.

References: imdb.com, whatculture.com, biography.com, comingsoon.net

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