Skip to main content

Meet Daveed Diggs, the Rappingest Rapper in "Hamilton"

Long before "Hamilton" brought hip-hop to Broadway, Daveed Diggs was an astoundingly talented rapper breaking rap's rules.

“What do you do?”

“I write for a hip-hop website. Album reviews, interviews, that kind of thing.” 

“Oh...have you seen Hamilton?!”

That’s a conversation I’ve had, verbatim, seven million times over the past year. Whenever I mention hip-hop (often to an older person) their response is now immediately to mention Hamilton. It’s made me realize just how insanely popular the musical is. That and tickets that cost more than my rent, Lin-Manuel Miranda at the GRAMMYs and the 100,000 Tony Awards they took home last night.

Hamilton is a huge moment for hip-hop culturally, but we haven’t written about it yet because it’s hard to cover a play you haven't seen. It's strange to be obsessed with hip-hop, have something be such a big part of the culture, and yet not being able to find a way in. But while we may not be able to cover Hamilton in all its revolutionary glory, today I realized that we can certainly talk about one if its biggest players, Daveed Diggs.

Beating out two of his Hamilton costars, Daveed Diggs has won the 2016 Tony Award for Best Performance by an Actor in a Featured Role in a Musical for his dual part as both Marquis de Lafayette and Thomas Jefferson in the Broadway smash.--

While playing two characters in a major Broadway production is incredible, for hip-hop heads - or at least the hip-hop heads who can't afford Hamilton tickets - I think his real rap achievement lies elsewhere. When I first heard about the play, I was skeptical. As stereotypically backpacker-ish as it may sound, I didn’t want to see hip-hop exploited and mainstreamed by vultures with no knowledge or care for the culture. The more I learned though, the more I came to realize that couldn’t be further from the truth. Groundbreaking, creative, and of course artfully assembled, Hamilton represented hip-hop to the fullest. But it helped to have Diggs on board because he is an artist with a real rap career that stretches back long before Broadway came calling.

Scroll to Continue



5 Songs You Need to Hear: Best of the Week

Press play on new tunes from Wizkid, G Herbo, Ayra Starr, Kaash Paige, and Ayoni.


yvngxchris Went From Recording on Earbuds to Viral Star

Rapper yvngxchris started off making songs on iPhone earbuds. Now, he's signed and constantly going viral.


5 New Albums You Need to Hear This Week

EST Gee, Nasty C, Idahams, Mura Masa, and KA$HDAMI all released new albums this week that you need to hear.

It’s no wonder Diggs was able fit Hamilton so perfectly, his solo stuff really displays an unconventional, left-field style needed to take hip-hop and make it a musical. Though that "Wash" beat knocks - kind of sounds a little Pusha T/Clipse-esque, no? -  it’s very slow and Diggs is equally as unconventional with his cadence and delivery. There’s no real structure, no hook, no set rhyme scheme or flow and yet the song flows so well. A lot of the time we judge rappers based on set standards - 16 bars over a soul sample, for example - but sometimes you need to judge them on how they defy those standards. This is one of those times. He doesn't just rap, he is a rapper. Though his solo work is worth checking out, you can grab the album here, Diggs is also part of a rap trio called clipping. (No, that's not a typo. It's clipping with a lowercase "c.")

"Summertime" was the first clipping. song I found and it's my favorite (so far). At first I wasn't quite sure what do do with it. It was cool, but very different and at first I wasn't quite into it, but when I digested everything, from the visuals to the beat's West Coast bounce, I became enamored with the quite loaded effort. Again, it defies any conventional sound and yet has that very traditional headnodic feel to it. While I loved "Summertime" after I settled into it, "Get Up" is another story. 

The entire beat is an alarm clock. The whole thing!  This is one of the most challenging songs I've encountered in a while and I mean that as a complement. Sometimes music needs to challenge our way of thinking and hearing. As an artist challenging listeners can be a tough task, you want to expand their mind and give them something to wrestle over, but at the same time, you need to have something for them to come back to. Just as that beat drives me crazy, I can't stop listening because Diggs is magnetic. That third verse is astounding! WOOOOO! I definitely need to give their CLPPNG album more time, but I can already tell this is one album I missed the first go-around.

As it turns out, Diggs music is as unique as his story. We've heard of rappers getting signed overnight, we've heard of rappers turned actors (and actors turned rappers), but have you ever heard of rappers getting their big break on Broadway? The whole time I was researching Diggs' rap career, as I was listening to "Summertime" for the 80th time, I kept thinking about how back in 2010, he had no idea it would lead to all of this. Earlier today Nathan dropped an article about "making it" as a rapper, and reading it, with CLPPNG bumping, I couldn't help but think about Diggs.

Five years ago he was a "struggle rapper" and now he is a Tony Award winner more famous that he likely would have ever been as only a rapper. It's a come-up story unlike any other. If we are going to cover Hamilton without seeing it, I can't think of a better way than spotlighting the unique story and music of one of its biggest players. 

Meet Daveed Diggs, the first Tony Award winning rapper in hip-hop history, and a rapper you need to listen to. 

Lucas Garrison is a writer for DJBooth. His favorite album is College Dropout but you can also tweet him your favorite Migos songs at @ItsLucas_G. Image via Instagram.



5 New Albums You Need to Hear This Week

EST Gee, Nasty C, Idahams, Mura Masa, and KA$HDAMI all released new albums this week that you need to hear.


Van Buren Want to Turn Brockton From Slept-On to Powerhouse

Rap collective Van Buren carry their city with them wherever they go. They break down how they're giving back to Brockton in a new interview with Audiomack.


5 Songs You Need to Hear: Best of the Week

Selections include EST Gee, Asake, Greentea Peng, Midwxst, and Prince Swanny.


5 New Albums You Need to Hear This Week

Get familiar with the latest works from Asake, NAV, Ari Lennox, TiaCorine, and Van Buren.


5 Songs You Need to Hear: Best of the Week

Yeat, Lil Baby, Govana, Kali Uchis, and KUR all released new songs worthy of your ears.


5 New Albums You Need to Hear This Week

Queue up new albums from Pi'erre Bourne, Erigga, TROD, Sha Ek, and PreyƩ.