10 Musicians Who Quit School/Work and Became Wildly Successful

by Anne T. Donahue

June 6, 2011

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The sun is shining, it’s finally nice outside, and the last thing you want to do is gaze from the confines of your office or classroom and dream of the days you should be having. So in celebration of the wondrous freedom of telling your boss and/or teachers to suck it, we’ve come up with a list of musicians who did exactly that. And while they may be high-school dropouts and masters of not giving a care, we tip our hats (WITHOUT CONDONING IT, WE SWEAR) to these ladies and gents who gave the conventional 9-5 the proverbial finger.

10. Cat Power

While we’re not about to give our blessing to leaving high school before grade 12, the artist-formerly-known-as Chan Marshall spent most of her childhood moving around before leaving high school and adopting the Cat Power moniker. One decades-spanning career later, and the “stay in school” motto loses a little more steam.

9. Kanye West

If his whip-smart prose hasn’t yet convinced you, perhaps Kanye’s scholarship to Chicago’s American Academy of Art will. True to West’s manic decision-making (see: Taylorgate), the burgeoning rapper transferred to Chicago State to major in English, then left school altogether to pursue—wait for it—music. Hello, College Dropout.

8. Lily Allen

High school dropouts look tame compared to Ms. Lily Allen who was expelled from her London high school for allegedly performing sexual favours on her classmates. A dropout at age 15, the singer vowed not to “spend a third of her life preparing to work for the next third of her life, to set herself up with a pension for the next third of her life,” and eventually moved on to record the smash album, Alright, Still. The rest can be found on Perez Hilton.

7. Dave Grohl

Not that you need to be convinced of Dave Grohl’s skill set or general awesomeness, but after leaving one high school (where he did morning announcements, thank you very much) to head to another, the Foo Fighters frontman gave academia the ol’ heave-ho, joining the DC punk band Scream, and offering this explanation: “I was seventeen and extremely anxious to see the world, so I did.” Did. He. Ever.

6. Courtney Love

After moving through several juvenile correctional facilities and gaining emancipation from her parents, 16-year-old Courtney Love ventured to the UK where she worked as a photographer for Hot Press and as a stripper. Following a trip to Tokyo that led to a particularly memorable (or the opposite) incident with heroin, the Hole singer returned to the US and took up with the Portland punk scene, thus beginning the controversial legacy we still can’t turn away from.

5. Jack White

If you already bow down to the alter that is Jack White, know that it could’ve gone differently: before opening his own upholstery shop, the former White Stripes frontman had plans to enter the seminary. And while Third Man Upholstery was financially viable, the endeavour didn’t last. Landing his first professional gig with Detroit band Goober & the Peas, we know how the rest turned out.

4. Peaches

Continuing on the road of “job-quitters vs. dropouts” comes Peaches (previously known as Ms. Merrill Beth Hesker) who once taught drama and music at the Associated Hebrew Schools of Toronto. Not that you necessarily need a recap, but suffice to say she’s since stopped (or merely succeeds brilliantly at hiding behind her makeup-clad stage persona).

3. Drake

Once upon a time, Drake was known only as Degrassi student Jimmy Brooks, the former basketball star shot by a classmate (landing him in a wheelchair and in a whole lot of emotional woe). Fast forward to 2011, and there may be way too many people here that he didn’t know last year, but thanks to syndicated Canadian TV, we still know exactly who the fuck he is.

2. Jay-Z

While quitting high school before age 16 may seem like “badass” personified, Jay-Z’s transition from crack dealer to billion-dollar mogul not only trumps any other abandonment of job confinement, but any other evolution entirely, proving that regardless of circumstance or what you’ve done (like, say, shooting your brother), you can indeed rule the world. Or have a wife that claims to.

1. Gregg Gillis (Girl Talk)

There comes a time when biomedical engineering just isn’t enough, and after graduating from Case Western Reserve University in Cleveland and going on to become an engineer, Gregg Gillis ditched the wide world of science to focus solely on Girl Talk, leading to quite a different social circle, we presume. Bill Nye would be so disappointed.

Tags: Music, Lists, Cat Power, Courtney Love, Dave Grohl, Drake, Girl Talk, Gregg Gillis, Jack White, Jay-Z, Kanye West, Lily Allen, peaches

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