I’m a big Mos Def fan. I consider myself a Day One supporter actually. I don’t have any recollection of his appearances on The Cosby Mysteries in the mid ’90s and I didn’t hear his debut single “My Kung Fu” until I went digging for old material in the early aughts but I’d like to think I was aware of Mos before most. I first heard him on De La Soul’s “Big Brother Beat” off 1996’s Stakes Is High and later on the remix to the title track — the B-side to “Itzsoweezee.” Then came Bush Babees’ “The Love Song” (1996), his own single “Universal Magnetic/If You Can Huh! You Can Hear” (1997) and Reflection Eternal’s “Fortified Live” (1997). I was sold.

1998’s Mos Def & Talib Kweli Are Black Star helped make him an underground favorite but he truly turned the corner with his 1999 solo debut, Black on Both Sides. The LP was critically acclaimed, earned a gold certification and featured excellent singles “Ms. Fat Booty” and “Umi Says” — the latter eventually appeared in a Jordan Brand commercial.

Again, I initially wasn’t aware of Mos’ acting chops so I was pleasantly surprised to see how good he was when I saw Spike Lee’s Bamboozled (2000). It turns out he was a trained actor. He was instantly credible unlike most rappers-turned-actors. Sure, Will Smith is still considered one of the biggest stars in Hollywood over two decades into his acting career. Ice Cube has been a staple in the film business for 20-plus years and there’s a number of other raptors (Ice-T, LL Cool J, Common, etc) who’ve made a mark in Hollywood. But in the early aughts, the influx of rappers appearing in movies was perceived as a marketing ploy to get a specific demographic into theaters or an unfortunate trend that took jobs away from real black actors. Samuel L. Jackson famously took a stand against rappers-turned-actors in 2002. “To take people from the music world and give them the same kind of credibility and weight you give me, Morgan Freeman, Laurence Fishburne, Forest Whitaker — that’s like an aberration to me,” Jackson told the Sacramento Bee. ”I know there’s some young actor sitting in New York or L.A. who’s spent half of his life learning how to act and sacrificing to learn his craft but isn’t going to get his opportunity … because of some actor who’s been created.”

Umi Says: A Deep Journey Through Mos Def’s Discography

Mos was an exception to Jackson’s rule. He had stripes. The original Pretty Flacko starred in an impressive string of quality films during the early aughts — appearing in the Best Original Screenplay-nominated Monster’s Ball (2001), Brown Sugar (2002), The Italian Job (2003), The Woodsman (2004) and earning a Golden Globe and an Emmy nomination for his role in HBO film, Something the Lord Made (2004). He also served as host of HBO’s Def Poetry Jam and starred in Pulitzer Prize-winning play Topdog/Underdog during that stretch. I remember thinking, “Mos is outta here when he drops his next album. Smith was on the verge of becoming the biggest movie star in Hollywood at the time but it still felt like Mos was inches away from reaching the center of the intersection between the music business and film industry. I’m an unapologetic Smith stan. I was a child when DJ Jazzy Jeff & The Fresh Prince came out so I never thought he was corny but they weren’t exactly Eric B & Rakim. And Will’s solo material reached new levels of cheese. Although, it feels like there’s sort of a retroactive appreciation for “Miami.” Mos was poised to become the standard with his sophomore album — a respected entertainer who juggles critically acclaimed and commercially viable material across music, TV and film. He was as capable of writing a perfect verse as he was of stealing a scene. He had EGOT (Emmy, Grammy, Golden Globe, Oscar, Tony) potential. Smith has two Oscar nods and DJ Jazzy Jeff & The Fresh Prince won the first rap Grammy but come on! Illmatic, The Chronic, Doggystyle, Ready to Die and All Eyez on Me were never nominated for a Grammy so…

George Clinton’s Co-signs Valid For Childish Gambino’s Awaken, My Love!

Mos teased a side experimental rock project called Black Jack Johnson — comprised of Dr. Know of Bad Brains, Bernie Worrell of Parliament-Funkadelic and Doug Wimbish and Will Calhoun of Living Colour — for years before scrapping it. The New Danger finally dropped in 2004 and I was disappointed, to say the least. “Sex, Love & Money” eventually grew on me but its replay value is questionable. “Sunshine” was dope. I can barely remember anything else off the album. It was panned by critics and it didn’t do well commercially. Mos’ musical output has been weird ever since. True Magic was the weirdest thing. It leaked and the physical version didn’t even have a cover. I did like “The Undeniable,” though. The Ecstatic was pretty good but it didn’t get the type of attention a Mos Def project deserves. For the record, I don’t think Mos ever fell off. I can’t help but think that there’s been an element of self-sabotaging to his career like he was getting too famous and made decisions that allowed him to live a normal life instead of taking him to another stratosphere. God forbid he reached a point where he couldn’t walk through Brooklyn without security. I can respect that. By the way, I never quite transitioned into calling Mos, Yasiin Bey, hence the numerous MD references.

I initially wasn’t a fan of Donald Glover a.k.a Childish Gambino. I was curious. I’d met him briefly during a visit to the XXL Magazine office (my former job) in 2011 and liked his energy. I remember seeing him perform in front of a sold-out crowd at Terminal 5 in New York City right before Camp came out and being shocked at all the white kids rhyming along to his every word. Meanwhile, very few of the black people I know knew he existed at the time. They didn’t watch 30 Rock or Community. I didn’t either. Well, I’ve seen 30 Rock countless times but I’ve never watched it religiously. Glover famously gained notoriety as a writer on 30 Rock and starred in Community. I heard Camp when it first came out and grew more intrigued. I didn’t love it but I knew there was something there. Donald was clever and I loved his perspective, most notably his very unique take on race.

In 2013, Because the Internet proved to be an impressive leap. Donald scored his first radio hit in “3005” and it featured several standouts, including my personal favorite Gambino song to date, “III. Telegraph Ave (Oakland).” Lead single “3005” had an interesting shelf life. It was first released in October 2013 but didn’t start gaining traction until the summer of the following year. That’s when I started hearing the people who previously didn’t know he existed, increasingly bring him up. The Kauia EP officially turned me into a fan. I thought “Sober” was a fantastic song and should have been a hit. “Pop Thieves” and “The Palisades” were also dope. I remember playlisting the hell out of “Sober” on Beats Music. I knew Donald could sing based on “3005” and “Telegraph” but the Kauia EP showed unprecedented range. I got a chance to see Donald do a few songs off the EP during an intimate performance shortly after the release. I was floored. Many rappers can hold a note but very few can actually sing. Donald wasn’t a studio singer. He was the real deal. I was sold.

There’s a two-year gap between Kauia, Awaken, My Love! and Atlanta but Donald somehow still felt omnipresent to me. He did star in Magic Mike XXL (2015) and The Martian (2015). Atlanta was an instant hit. The premiere episode drew 1.8 million viewers, the best premiere tune-in for a basic cable comedy since Inside Amy Schumer in 2013 and the biggest comedy debut in FX history. Meanwhile, critics praised the new series, Black Twitter applauded and hipsters approved.

Gambino released his third album, Awaken, My Love! — a surprising funk-inspired LP — roughly three months after the Atlanta premiere. The album sold 72,000 in its first week and debuted at No. 1 on the R&B album chart. The album’s best song and lead single, “Redbone” finds Gambino singing a grainy falsetto that would make Prince proud. His incredible Jimmy Fallon performance of “Redbone” confirmed that there were no special effects used to enhance his vocals. The album features a number of other standouts, including “Me and Your Mama,” “California” and “Terrified.” For me, the combo offering of Atlanta and Awaken, My Love! cemented Donald Glover as the most talented entertainer of his generation. No one comes close. His range is too great. Donald kick-started what will likely become a year-long victory lap when he won Best Actor in a Musical or Comedy TV Series at the Golden Globes last month. Atlanta also took home Best Television Series — Musical or Comedy. He’s likely to score a Primetime Emmy nomination later this year and Awaken, My Love! is a shoe-in for Best Urban Contemporary Album at the Grammys next year.

Yasiin Bey & Ferrari Sheppard Deflate Expectations With December 99th

As a Mos fan, I was initially hesitant to write this piece, but the more I think about it the more I wonder, is Donald Glover a.k.a. Childish Gambino becoming what Yasiin Bey f.k.a. Mos Def should have been? They don’t exactly mirror each other but there are a few similarities between their career paths. Mos is hilarious but he’s no comedian. Although, footage of the Brooklynite doing a stand-up comedy show surfaced in 2015. In some ways, Donald’s career arc is arguably more impressive. Mos was the picture of cool from the start and his approval rating continued to spike with his growing profile. Gambino was initially labeled a nerd. It’s no coincidence that his 2013 Netflix stand-up comedy special was titled Weirdo. Black kids initially didn’t fuck with Gambino. Hipsters didn’t initially fuck with Gambino. Sure, he played Coachella in 2012 but take a look at the Pitchfork reviews of his first two albums. Brutal! Plus, I got first-hand confirmation from an indie authority that the hipster set wasn’t fond of Gambino at the time. Donald managed to win over black folks and hipsters at the same time. That’s fucking impossible!

I think Mos Def could care less what I wanted him to be. He always marched to the beat of his own drum so my question may not have been fair. Maybe this is exactly how Mos drew it up. Maybe he didn’t want it. I recently had a great conversation with my homie Fam (Donald’s manager) and Donald and I gave them a heads up that I was thinking of writing this piece. Based on our convo, I got the impression that Donald wants it and is definitely going for it. He’s set to star in Spider-Man Homecoming later this year and he recently got cast as Lando Calrissian in the Han Solo origin story. Plus Atlanta should be back with a second season soon. Is Childish Gambino becoming what Mos Def should have been? No! He’s evolving into a dual threat and showing us a repertoire we haven’t seen before. It’s gonna be fun to watch.

This piece was originally published on Medium. Follow him @carlcheryam & medium.com/carlchery.