Skip to content
  • Essence GU
  • Beautycon
  • NaturallyCurly
  • Afropunk
  • Essence Studios
  • Soko Mrkt
  • Ese Funds
  • Refinery29
  • WeLoveUs.shop
  • 2026 ESSENCE Festival Of Culture
  • Celebrity
  • Fashion
  • Beauty
  • Lifestyle
  • Entrepreneurship
  • News
  • Shopping
  • Video
  • Events
  • Subscribe
Home • News

18 Singers Who Are Too Cool For School

If the music business was high school, this group of artists would be the clique of cool kids everyone wanted to hang out with. Their unique styles, both in the booth and on the red carpet, make them stand out from the crowd.
By Taylor Lewis and Jolie A. Dogget · Updated October 27, 2020
Getting your Trinity Audio player ready…
01
Frank Ocean

In 2012, Frank changed the game with his Channel Orange album. Exploring themes like religion and his own bisexuality, he ventured to where no R&B artist had gone before. And his hard work paid off. He was nominated for a Grammy that year (remember when he whistled during his performance?) and was featured in songs by artists like Kanye West and Beyonce. So after a quiet three years, it’s no wonder that we’re craving another album from him. His new album—Boys Don’t Cry, due out in July—can’t come soon enough.

You Gotta Listen To: “Bad Religion“

18 Singers Who Are Too Cool For School
Getty Images
02
FKA Twigs

From her baby hairs to her  FKA Twigs and her ethereal sound are the height of coolness.

You gotta listen to: “Two Weeks“

18 Singers Who Are Too Cool For School
Getty Images
03
Luke James

Luke James has burst from the background into the spotlight with his unique style and enviable vocal range that he used to once sing backup for Tyrese Gibson.

You know you gotta listen to: “I Want You“

18 Singers Who Are Too Cool For School
Getty Images
04
Solange

She’s the queen of not caring what people think about her. She has never felt pressured to follow in her big sis’s footsteps, giving her the freedom to create the bubbly tunes that give us life for days. 

You Gotta Listen To: “Sandcastle Disco“

18 Singers Who Are Too Cool For School
Getty Images
05
The Weeknd

We’ve been blasting The Weeknd ever since he dropped “Wicked Games” in 2012. We fell in love with his heartfelt lyrics and his uber-sexy falsetto. And his music videos? Sensual and addictive. 

You Gotta Listen To: “Wicked Games“

18 Singers Who Are Too Cool For School
Getty Images
06
Childish Gambino

The triple threat (rapper, actor and comedian) excels at all of his crafts, but it was his eclectic verses that first grabbed our attention seven years ago. It takes a very talented individual to blend elements of rock music into a rap, but Childish, whose real name is Donald Glover, does just that. 

You Gotta Listen To: “Freaks and Geeks“

18 Singers Who Are Too Cool For School
Getty Images
07
Kanye West

You didn’t think we’d forget Kanye, did you? He might be mainstream, but he’s still mighty. His most impressive feat? Inventing “rap ranting”—you know, rapping about all the wrongs in the world over a hot beat. Never change, Kanye. Never change.

You Gotta Listen To: “All Falls Down“

18 Singers Who Are Too Cool For School
Getty Images
08
André 3000

Andre has always made it a point to embrace his African roots, and he has used his platform as a public figure for good (he’s constantly urging young people to register to vote!). More than 20 years after breaking into the industry, he has maintained his signature style, his throaty voice and his progressive lyrics. Plus, his hats and bowties are always on point.

You Gotta Listen To: “Pink and Blue“

18 Singers Who Are Too Cool For School
Getty Images
09
Jidenna

Also known as the Swank Master of Ceremonies, Jidenna is nothing but unique in both fashion and sound.

You gotta listen to: “Classic Man“

18 Singers Who Are Too Cool For School
Getty Images
10
Janelle Monáe

The 29-year-old singer has flawlessly branded herself (seriously, we wish we could rock the menswear look like she does), and she’s guaranteed to keep you on your toes. Just when you think you know her, she goes and drops a song like “Yoga”: unexpected and brilliant.

You Gotta Listen To: “Tightrope“

18 Singers Who Are Too Cool For School
Getty Images
11
Mali Music

Mali Music is seriously changing the gospel game. The Grammy nominated singer is spreading a message of love and positivity in every track he puts out.

You gotta listen to: “Beautiful“

18 Singers Who Are Too Cool For School
Getty Images
12
Prince

He’s the original kool kid. He’s the headmaster of Kool University. He’s the reason why we have all these other brilliant experimental artists. That is all.

You Gotta Listen To: Every. Single. Song.

18 Singers Who Are Too Cool For School
Getty Images
13
Jhené Aiko

Her soft, raspy sound is the new definition of easy listening

You gotta listen to: “Stanger“

18 Singers Who Are Too Cool For School
Getty Images
14
Drake

We don’t know if a hip-hop artist has ever given as many feels as Drake does. He has earned the respect of some of the hottest in the industry, but he’s not afraid to wear his emotions on his sleeve. And we love him for that. 

You Gotta Listen To: “Marvins Room“

18 Singers Who Are Too Cool For School
Michael Tran
15
Common

Common is like the People’s Rapper. He has turned into an expert at bringing social injustices to light (he just won an Oscar for it!), and he hasn’t let his fame change that. Instead of hopping on the mainstream’s bandwagon, people have hopped onto his.

You Gotta Listen To: “I Used to Love H.E.R.“

18 Singers Who Are Too Cool For School
Getty Images
16
Erykah Badu

The fairy godmother of keeping it real, Erykah Badu is one of the earliest examples of avant-garde music from the soul.

You gotta listen to: “On & On” (if you haven’t already)

18 Singers Who Are Too Cool For School
Getty Images
17
Daley

The British singer-songwriter has made a niche for himself after hitting it big on “Alone Together” with Marsha Ambrosius. Always rocking his curly mohawk, Daley never strays far from his signature mellow sound, but he can hold his own in the music world.

You Gotta Listen To: “Alone Together“

18 Singers Who Are Too Cool For School
Getty Images
18
SZA

SZA is wise beyond her years with vocals beyond belief. Her alternative sound will transport you to another listening dimension.

You gotta listen to: “Babylon“

18 Singers Who Are Too Cool For School
Getty Images
19
Kendrick Lamar

Kendrick Lamar stays true to West Coast style by spinning tales of the struggle and the triumphs of a young Black man in every verse of every track. 

You gotta listen to: “M.A.A.D. City“

18 Singers Who Are Too Cool For School
Getty Images