Once upon a time, a Wu-Tang Clan name-generator gave Donald Glover the rap name Childish Gambino, leading to his first mixtape, Sick Boi, as a 25-year-old who’d already written for 30 Rock and co-founded an OG YouTube sketch team, Derrick Comedy.
Gambino self-released four more tapes before joining the indie label Glassnote Records to start selling music in 2011 with a glossy EP and the full-length Camp. While praised for his writing, acting and stand-up comedy work, Glover continually clawed for respect as Gambino, held at the margins of the mainstream and often derided in the hip-hop blogosphere. All the while, an intensely devoted following grew online, comprised largely of kids as “nerdy” as Glover, ones who’d see him live any chance they got and maintain fan Tumblrs at home.
At the end of 2016 — the same year Glover created, directed, wrote, and starred in FX’s award-devouring Atlanta — Childish Gambino at last became a musical critical darling with the daring (and rap-less) “Awaken, My Love!” Here, we enjoy the 33-year-old’s best songs released in his near decade on the scene.
15. Childish Gambino – “Backpackers”
Saddled with as many flat and problematic lines as anything on debut album Camp, this one pops for being Gambino’s most irate critique of his critics. It’s also a completely unique production in his discography, something Wu-Tang themselves might’ve fucked with.
14. Childish Gambino – “Almost There”
Glover’s pre-Camp work was marked by an ultra-nasal voice and a lot of flows nakedly cribbing from Lil Wayne and Jay-Z, but once in a while the DNA of the artist he’d become bubbled up. His sophomore drop Poindexter arrived in 2009, the same day NBC’s Community premiered, and with it came this genuinely anguished, fantastically rapped plea to an ex. “I never ever thought that I would be scared,” he admits, “Of living in a world where you are not there.”
13. Childish Gambino feat. Bun B – “R.I.P.”
Syrupy synth underscores a killer Royalty mixtape collab between the Houston hero Bun B and Atlanta outcast-turned-idol Gambino, while an airy sample from French house DJ Kavinsky adds a layer of fun.
12. Childish Gambino – “Be Alone”
Fears and insecurities have been standard in hip-hop for a long while now, but opening an EP by falsetto-belting “I don’t wanna be alone” with this level of anguish and earnestness just wasn’t something hip-hop heavy hitters did in 2011. It stays on topic from there, mulling and dreading isolation, rejection and two-faced Hollywood minions, while gifting us with the gem, “They laughed at my rise like my motion was funny/ Ashy to classy, my lotion is money.”
11. Childish Gambino – “Candler Road”
All the badassery of the ATL-centered rappity-rap STN MTN mixtape is captured on this two-parter, the most natural moment for host DJ Drama‘s ad-libs, suffused with a freestyle vibe both bars-wise and melodically: “I don’t have words for this part/ But I know it should sound like this/ Dun da dun dun dun dun/ Love you all the time.”
10. Childish Gambino – “Me and Your Mama“
The first taste of “Awaken, My Love!” (which soon became the album opener) was audacious, with Gambino himself — missing in action for a couple years — staying quiet till the two-minute mark. When he descended upon the atmospheric live-instrumental, quietly choral intro, it wasn’t to rap but to deliver a tortured blues roar referencing a relationship and a new child that the press knew nothing about. The extended decrescendo ending — also sans vocals — is as breathtaking as the build-up.
9. Childish Gambino – “Kids”
This late Camp cut lightly swirls tinkling xylophone with soft strings to juxtapose the complications of adult love and the pure simplicity of childhood crushes. “If we were kids/ I’d want to give you everything that you would want,” Glover coos on one of the best hooks of his career at that point, only to have it gorgeously doubled by a violin throughout.
8. Childish Gambino – “Pound Cake Freestyle”
A big part of what kept Gambeezy at the margins of music until “Awaken, My Love!” was our culture’s “There Can Only Be One” problem. Why focus on Donald Glover when another emo actor-turned-rapper-singer was in the top spot and putting out new stuff nonstop? So when Childish Gambino hit Sway in the Morning in a furry Russian hat to casually body Drake‘s godly Nothing Was the Same beat, rap’s axis tilted a little. The icing on the cake (“cake-cake-cake-cake-cake”) came when Sway assumed Glover was done and ready to chat again… only to get cut off by more fire.
7. Childish Gambino – “I. Crawl”
It’s a real magic trick to have your album’s first set of bars be uniformly groan-worthy (“Still put it down like the family dog”; “Explain it all/ Ferguson”) yet have them set up a monster Kickstarter on a classic LP (Because the Internet, in this case). Glover slam-dunked it by going outside his usual circle to collaborate with veteran producer duo Christian Rich on a busy, bashing beat with tweaked-out vocal samples and a graceful orchestral bit.
6. Childish Gambino feat. Chance the Rapper – “I. The Worst Guys”
We’d dwell more on the mystery of why Chance is solely here to murmur the words “all she needed was some” a bunch of times, if the Because the Internet standout wasn’t so brilliant regardless. It’s almost an entire summery emotional state unto itself, a prime example of Gambino and his Swedish right-hand man, film and TV composer Ludwig Göransson (Black Panther, Community, New Girl) doing their inimitable thing together.
5. Childish Gambino – “Pop Thieves (Make It Feel Good)”
Kauai EP opener “Sober” is an all-timer, catchy with a great video, but immediately after it comes the pop-themed project’s best and busiest bop. It’s a moment where Glover crushes a genre so deftly you can’t help but imagine an alternate career as a king of Top 40 radio. Also: a snatch of spoken word from Jaden Smith at the end!
4. Childish Gambino – “Secret Track”
The best iteration of “3005” isn’t the Because the Internet original or the minimalist “Beach Picnic Version” on Kauai, it’s the spinoff that stayed buried inside the code for Gambino’s 72-page Because the Internet online movie script for nearly a year before a Redditor was able to hack the Matrix. It’s remarkable Glover was content to hide such a marvel away, potentially to never be found. The way it loosely plays around with the pieces of “3005” and adds brand new bits feels like the days when hip-hop remixes were legitimately tweaked and redone, not just the same old single with a new guest verse tacked on.
3. Childish Gambino – “Stand Tall”
Shiningly hopeful, the “Awaken, My Love!” closer features some of Glover’s most passionate vocals gliding over a choir, flute and the last of the album’s wavy guitar work. The acoustic, radiant final section feels like the crew celebrating the last session of a massive achievement.
2. Childish Gambino – “IV. Sweatpants”
This can sit alongside Kanye West’s “Can’t Tell Me Nothing,” Drake’s “Trophies,” or Kendrick Lamar’s “Backseat Freestyle” as an ultimate pump-up rap (“Don’t be mad ‘cause I’m doin’ me better than you doin’ you”) with all the bells and whistles. It’s one of Glover’s most confident and acrobatic hip-hop performances peppered with goofy little moments like the pause to correct his own lyric (“Fiskers don’t make noise when they start up, just so you know”), gold lines like “Yeah, you got some silverware, but really, are you eatin’ though?/ Breakfast, lunch and dinner’s for beginners, you ain’t even know,” and gleeful references on references, as far and wide as Ben Folds Five, Sweet’N Low, emo, Socrates’ pederast, Jeff Goldblum’s The Fly, IKEA and Sofia Coppola.
1. Childish Gambino – “Redbone”
Funny that Gambino’s best single ever should come in the middle of “Awaken, My Love!”, a record that works most masterfully as a whole, trippy, start-to-finish experience. This one will end up on an array of best-of lists for many years to come and it’s got the bragging rights of being the official musical torchbearer for one of the most potent phrases of our age: stay woke.