15 Celebrities Who Tried & Failed To Be Rappers

This isn’t a list of struggle rappers (we could go on for YEARS about those…and then we’d have to break it down by city, by locality, by nightclub, by Instagram followers…), but a list of people who are otherwise reasonably employed, well-known, and who have “respectable” reputations who decided to try their hand at the dozens.

(Nick Lachey isn’t the first to do this…and at the rate things are going, he certainly won’t be the last…)

Unfortunately, they failed…and miserably. Fortunately (for us), they have left behind a record of their buffoonery for all of posterity to admire (and, in this case, laugh at). Here, then, is our hilarious list of people who tried to be rappers — and failed, miserably.

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Photo: WENN.com

15. Terrence Howard

He was so convincing in Hustle & Flow that it was hard to believe that he wasn’t a rapper IRL. Fortunately, after Hustle & Flow, he decided to stick with acting.

14. David Faustino

Bud Bundy really thought that his glory as a rapper named D’Lil would be lost in the annals of history. He was fortunate to do this at a time when YouTube & Instagram didn’t exist (the early 1990’s)…but unfortunately for him, nothing stays dead forever thanks to the Internet. This is his “hit single” called “I Told Ya,” and for those who really wanted to know, there’s also a “metal remix” of the track. Hey, it was the 90’s…it was a very different time…

13. Karl Rove

It wasn’t enough to be part of an Evil Empire known as the Second Bush Administration…no, Karl Rove had to try to be a rapper, too. Peep MC Rove’s attempt at Hip-Hop, where he takes the HOP part literally…

12. Shia LaBeouf

It should come as no surprise that Hollywood’s favorite plagiarist has also tried to steal the basic elements of the Hip-Hop culture that will never embrace him. As a white person, I can tell you with absolute certainty: no, we don’t want to claim him either. (The fact that he does this for EIGHT MINUTES brings a whole new meaning to the words “Eight Minutes of Death”…)

11. Ed McMahon

The late co-host of The Tonight Show with Johnny Carson is like your Dear Old Granddad: someone who means well, but who’s been besotted by dementia & old age and thus merits pity. In this commercial for FreeCreditReport.com, McMahon raps about being broke…and you’ve gotta appreciate his self-deprecating honesty. Would be nice if other rappers would have that same integrity…

10. Gwyneth Paltrow

Pepper Potts puts the “milk” in milquetoast — she’s so vanilla, even Chris Martin of Coldplay couldn’t deal with it. (Too soon for the “conscious uncoupling” jokes?) Despite her attempts at trying to be “down with the brothers” by saying the N-word, being “besties” with Jay-Z & Beyonce, and singing “Straight Outta Compton,” she will never — EVER — be Hip-Hop.

9. Brian Austin Green

This is the second star of the 1990’s that tried his hand at a rap career. No one knows what happened in the 1990’s to make rich white folks decide that they, too, could be rappers (we’re guessing it had something to do with Vanilla Ice), but it happened, and there’s nothing anyone could do about it except laugh. Here’s former 90210 star/current Megan Fox husband Brian Austin Green singing “You Send Me,” from his one-and-only (thank God) Hip-Hop album, One Stop Carnival.

8. Tina Fey

Is Tina Fey funny? Yes. Is Tina Fey a rapper? No. But bless her heart for trying. And further bless Childish Gambino for giving her a platform to try…

7. Tom Hanks & Dan Aykroyd

The only two names that could be more milquetoast than the aforementioned Gwyneth Paltrow are Tom Hanks & Dan Aykroyd. I think we can blame this 1987 poop-show for Chet Haze’s (a/k/a Chet Hanks, son of Tom, student at Northwestern University) current struggle rap career.

6. Rosie O’Donnell

No. Just. NO. Who did this? Who said this was a good idea? Why, Lord, WHY have you forsaken us?

5. The Andover Academy Students

For those who don’t know, Phillips Academy Andover — sometimes simply known as The Andover Academy — is the breeding ground for the Illuminati (not the kind Jay-Z raps about…the REAL kind…), allegedly. It’s the oldest boarding school in the United States, and per its own admission, admits to being both the home base of several secret societies AND having said societies be an open part of school life. So when you hear of several of their uber-privileged students trying to have rap careers, it really makes you wonder if these rumors are true…

4. Natalie Portman

In Padme Amidala’s defense, she wasn’t necessarily trying to have a rap career when she did this rap song on Saturday Night Live. But, as things like this are wont to do, it became a viral Internet hit…and it was actually funny, unlike many other things that SNL has been putting out as of late. But it led to Natalie being invited to do other rap songs…which wasn’t funny at all.

3. Shaquille O’Neil

A word of advice: skills on the basketball court DO NOT translate into skills in the booth. Shaquille O’Neil, we’re talking to you.

2. Oprah

House Mother Oprah was the first one to take rap music to task early on in her career. Now, of course, she recognizes the error of her ways (especially when she realized how much more money she could make by becoming BFF’s with Jay-Z & 50 Cent), and has decided to try her hand at 16 bars. Adorable.

1. Justin Bieber

The border between the United States & Canada is the largest undefended border in the world…which is why it was easy for Da Beebz (as he would like to be known) to sneak across and poison our ears, first with his so-saccharine-we’re-getting-diabetes pop music, and now with his dear-God-make-it-stop rap music. Teaming up with Birdman isn’t helping matters any. Baby, baby, baby…ugh.

Follow Bernadette Giacomazzo on Twitter at @berngiacomazzo