When it comes to celebrating Black artists and promoting Black culture — from comedy to music to theater — there's no place quite as famous as the Apollo Theater in Harlem, New York City. And when it comes to launching the careers of famous Black musicians, no Apollo event can make or break a star like the venue's Amateur Night, a raucous revue of up-and-coming talent with a notoriously opinionated crowd and even a so-called "executioner," who sweeps unpopular acts off the stage with a broom.

The Apollo's Amateur Night has launched the careers of many a diva and nurtured musical styles as varied as hip-hop and jazz. Below are some surprising artists who went from good to great — or great to legendary — at this iconic venue.

 

Ella Fitzgerald

 

 

Okay, okay — it might not be surprising that jazz legend Ella Fitzgerald got her start at the Apollo. After all, she's one of the theater's most celebrated success stories and a North Star in the venue's dizzying array of legends. But many people don't know how close Fitzgerald came to not being a star.

Orphaned at the age of 15, Fitzgerald survived an asylum and a brutal reformatory school, where she was denied a place in the choir because of her race. When she attended the Apollo's Amateur Night in 1934, she was homeless and a high school dropout. She and her two girlfriends put their names in the hat as a dare, never thinking they would be called on stage — but as luck would have it, Fitzgerald was.

Originally, Fitzgerald had planned to dance, but she was called up right after a stellar dance number and balked. Not sure what she'd do instead, she told the audience that she sang a little and tried out a few rough bars of the song, "Object of My Affection," and got booed by the disapproving crowd. But with a bit of help from the emcee, she tried again — and the rest is history. 

Fitzgerald became the first Black woman to win a Grammy, followed by 12 more throughout her decade-spanning career. She sold a mind-boggling 40 million records and helped establish jazz as both a uniquely African American and quintessentially American art form because she dared to sing instead of dance.

 

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Questlove 

 

  

 

The drummer and co-frontman of The Roots didn't get his hip-hop start at the Apollo. Raised by two musical parents, who were also at the forefront of soul and doo-wop groups in Philadelphia, Questlove grew up backstage and began drumming on stage at the age of 7 and directing music by age 13. But even if the Apollo didn't launch the hip-hop artist's career, it certainly shaped his view of the music world.

While backstage at his dad's reunion concert at the Apollo, Questlove remembers that another singer came on stage to tell his dad that his car was being taken to pieces for parts in the back alley. Earlier, Dinah Washington told his dad to lose his white gloves — "too minstrel" — and his mother warned him that anyone who played at the Apollo had better be good or be prepared to literally have rotten tomatoes thrown at them. 

Questlove's first impression of the Apollo was fear, but the scene set a high standard in his mind. When he played the Apollo years later, he knew he had to bring his A-game. Unfortunately, the man who opened for them, a wild rapper Questlove had met at a local barbershop, failed the test and got the proverbial tomato treatment. But The Roots killed it, and Questlove went on to become one of the most groundbreaking, genre-bending artists in the hip-hop game, making music with everyone from Amy Winehouse to Fiona Apple and scoring The Roots an ongoing gig as the house band for the "The Tonight Show Starring Jimmy Fallon."     

    

Dave Chapelle

 

 

Part of the appeal — and terror — of Amateur Night at the Apollo is the crowd: a notoriously unforgiving mix of teenage kids with big dreams, cocky upstarts, and even established movers-and-shakers who will boo anyone.

One of the comedians who learned this the hard way was Dave Chapelle, the erratic but almost unerring genius with a moxie that can only come from hard faith in his talent. But Chapelle's first showing at Amateur Night in 1989 had none of the signature traits we associate with the comedy legend today.

Chapelle had been rising in the late-night comedy scene and felt sure of his talent. But when he went onstage, he totally and utterly...flopped. His jokes weren't working; he kept staring at his shoes. And the audience hated it, booing him through his entire set.

Many comedians would have taken this as a signal that their career was over before it even started. But for Chapelle, his early flop at the Apollo spurred him on. Up to that point in his career, he had always feared failure. Before he went on stage that night, his friends asked him: what happens if you're not funny? But after the show, Chapelle knew: He'd failed, and he was still alive. The audience had delivered on his biggest fear, and he'd survived it. After that, the comic was fearless, booking back-to-back gigs at all the biggest clubs and attaining comedy superstardom and a lifelong following — haters be damned.

 

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Joe Gray

 

 

Sometimes stars come from unlikely places. Once the head carpenter and stagehand at the Apollo, who unloaded trucks for stars like Stevie Wonder and Whitney Houston, Joe Gray earned his place on the stage when iconic New Yorker and Apollo audience member Eva Issac heard him singing.

She asked Ralph Cooper, founder of Amateur Night, to listen, who then invited Gray to headline that evening. He started performing the Apollo theme song and other cover songs at Amateur night — and the crowds didn't hold back, at first booing him before embracing him as a fixture of the theatre.

After that introduction, he was known as "The Set It Off Man" and stood on the Apollo stage more than any star in the world, setting off Amateur Night every night until his retirement in 2019

 

H.E.R.

 

 

Performing at the Apollo at any age is a huge moment in any artists’ career, but a few singers got their big chance on stage as kids. Lauryn Hill got booed at age 13 (but still powered through her performance), and H.E.R. performed Aretha Franklin’s “Freeway of Love” on the iconic stage when she was only 10 years old. 

The Grammy-winning “Hard Place” artist, whose real name is Gabriella Wilson, wrote poetry when she was young. Recognizing her talent, her mom collected her poems, published them, and submitted a tape to perform at Showtime at the Apollo. Her audition tape was selected, and H.E.R. made her first trip to New York City — and the first step toward becoming the successful R&B artist she is today

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