Diallo Riddle spins a thoughtful, versatile style of comedy

Photography: Ricky Middlesworth; Grooming: Andrea Pezzillo; Styling: Michael Mann

Photography: Ricky Middlesworth; Grooming: Andrea Pezzillo; Styling: Michael Mann

Chad White

When it comes to working in comedy, it’s best to be versatile in nature. Most comedians do standup and write scripts. Many do improv along with acting. Others handle the day to day tasks of producing. But only a handful dip their toes into the music world.

Diallo Riddle is one of the few comedians who can do it all. From producing to writing and now acting, he’s conquered every facet of the comedy world. His latest venture includes being a cast member of the show Marlon on NBC where he takes a backseat to behind the camera tasks and moves to the forefront of the action. He’s also a DJ, which is cool.

I recently had a conversation with Riddle about his new role, writing and the city of Atlanta.

You have apparently been in my life via TV for years and years now. I didn’t know you were a Chocolate News writer!

Diallo Riddle: [laughs] Should we talk about it? Let’s talk about it!

What was that experience like?

Riddle: It was very weird. My writing partner, Bashir [Salahuddin], and I were writers on Chocolate News. It was our very first job in TV. The only thing we’d done before that is…a video that went viral in a 2007 sense. That just means we got two million views on YouTube which nowadays would get you kicked out of some clubs. [laughs] But, back then, doors would open for a video with 2,000,000 views. We got an interview over on Chocolate News because our video was slightly political. It had a lot of black faces in it so people were like “Who are these guys?”

We always loved [David Alan Grier] (DAG); we always wanted to work with him. He saw us, liked us, we came on board. But we came on board the season late. I feel like they’d already shot all the verbose…all of the pretapes I should say. We looked up and we were in a room full of experienced writers and Jeremy Bronson [laughs]. So really it was the first real comedy TV job for both myself and Bashir and Jeremy Bronson, who is now the showrunner on The Mayor.

It’s just sort of one of those weird confluence of events. After we left Chocolate News, we ended up at [Late Night with] Jimmy Fallon and so did Jeremy Bronson. So Jeremy Bronson went wherever we went for a couple of years by nothing more than coincidence. Chocolate News was crazy, man. Chappelle was gone. I think everybody was expecting every show with a black face on Comedy Central to sort of replace Chappelle’s Show which had left five or four years earlier. There was a lot of pressure on that show to be great.

Also, we were the brand new writers in the room. I remember we were doing punch up on a script, you know, with the whole writers room sitting around a table, looking up at a screen. And there was a joke about somebody having a big butt and the punchline was like “Jennifer Lopez.” And I remember I said “Hey guys, JLo jokes are fine but what if we made a Kim Kardashian [joke]?” And nobody pitched a Kim Kardashian joke in early 2008.

It feels like a hundred years ago. You forget what things weren’t on everybody’s radar in 2008. I remember one of the executive producers looking at me and being like “That’s good! That’s way better!” It’s insane that was only 2008. But we were the new guys in the room – we didn’t get many jokes on the air. For years we joked that when we come across somebody that’s like “I love Chocolate News!” we were like “Oh, we didn’t get that much on the air...” And if people come by and they’re like “I hated Chocolate News!” [we were like] “We didn’t get much on the air!” It’s a lose-lose situation. We can’t claim credit for it. It’s one of those things. It was our very first gig.

Here’s the good news: we had a great relationship with DAG then and we continue to have a great relationship. When I booked Marlon, one of the first people I saw at an NBC event was David Alan Grier. He came up and gave me a hug. He was like “Man, what you think you doing on TV?”

[Both laugh] That’s so crazy! You’re going to be the next DAG! It’s insane.

Riddle: [laughs] Man, I wish! That dude’s had a great and storied career. I’ve been a fan of his since In Living Color. The idea that I’d eventually work for him was a dream come true. The fact we got to do NBC press junket together when he was doing [The Carmichael Show] and I was doing Marlon was super surreal. Beyond surreal.

Since you’re on this television show and you’re not behind the camera writing, how has that transition been for you?

Riddle: It was crazy at first. There were times we would finish rehearsal and the head writer would be like “Alright guys. Let’s head on up,” talking to the other writers. I’d be like “Alright. Man, we’re going to be here tonight. I can feel it.” [laughs] They’d be like “No, Mr. Riddle. Do not follow us.” You can take it one of two ways. They want to protect the talent or “we don’t want your ideas.” It was trippy not being a part of the writer’s room. But I kind of loved it because I’ve never gotten to flex strictly an actor’s muscle. Truthfully, it’s all so very generous.

It all comes from the top. Marlon’s so generous and open to ideas that I found – especially as the season went along – if we were doing the third take and we’d already gotten the script, then I could easily go to the writers and say “Hey, what do you guys think if I said ‘blah blah blah?’” They’d be like “Oh yeah! Do that! Do that!” As the week went on, I would be in my dressing room, scribbling my notes in the margins. Who knows? I haven’t even seen any of these episodes yet. It’s going to be new to me what they kept in and what they had to cut for time. I’m going to be watching every episode – as should America – not knowing what’s going to happen next.

Speaking of not knowing what’s going to happen next, this is a sitcom – it’s got a live audience. What is the feeling of the instant gratification of a joke landing?

Riddle: Instant gratification! Man! I can talk about it. I’ll tell you. I did two pilots for HBO. I did two seasons on Silicon Valley as a lawyer for Hooli. I’ve lived in that single camera world where you say your joke…at most you’ll get a grip to snicker but then people get mad at him because he could ruin the shot. Single camera is all about repression. Everybody has to pretend like what you just did didn’t happen to protect their job. The thing I love most about a live studio audience is that you know immediately if a joke worked or not. And also, quite frankly, one in the six of the cast members on the show is a ham! The children are hams too. We eat that up.

There’s something wonderful about getting the laughs, letting it hang out there just a little bit, and right before it dies down, you hit them with a second joke. It goes right back to my favorite episodes of Seinfeld. Going all the way back to The Cosby Show, I didn’t know that I loved working in multicam world. But, now that I’ve done it, it’s going to be hard to do anything else. I love it. It’s something accessible about 99 people sitting out in that audience laughing, going crazy and having a good time. It feels more like a party. It feels like you’re getting compensated to be in the ultimate stage play. It’s so much fun.

Right? Multicam is a job that has so many tasks. When you’re done, you’re done. For single cam, when you need to reshoot something, you gotta come back instantly. With multicam, it’s a 9 to 5 job basically.

Riddle: Yes, that’s 100% true. There was one scene in particular that, in rehearsal, it felt one way and for whatever reason it felt completely different – just a little bit off. I remember – I wasn’t one to make a habit out of this – I did ask the director “Can we do one more take? I know you don’t usually do four or five takes…Let me get a fourth take here.” And so they were like “Yeah. Absolutely.” And then, in that fourth take, I was determined to recapture what I felt as Stevie – my character – in those rehearsals. I’m so glad I did because I know for a fact the head writer called me. He’s like “I’m really glad you asked for that last take. That’s definitely the one we’re going to use.”

When you shoot it for single camera you think “We’ll go back. We might get this in a reshoot if it doesn’t work today.” But with [this show]…all the cameras are there, all the actors are there; you better get it. And I think that little bit of a challenge made that made it even more electric.

You spoke a little bit on sitcoms of television’s past. Have you been channeling any characters from those shows specifically in order to help you with your first time multicam work?

Riddle: I think it’s inevitable that you’re going to think about some of your favorite multicam moments of the past. It’s such a specific medium and the timing is so different than single camera where you just toss off the funny line. It’s the opposite. You have to leave it floating out there for people to hear that joke sometimes. I think it’s inevitable that I was probably thinking about some of my favorite sitcom characters.

By the way, not all of them are from the 80’s and 90’s. I know I mentioned the Cosby Show and Seinfeld…but one of my favorite recent multicams was How I Met Your Mother. I felt like those actors brought a new life and way of doing the multicam format in a way that didn’t seem like I was trying to be a secondary guy on Taxi. It’s not the Mary Tyler Moore Show anymore and I thought a lot about How I Met Your Mother and some of the other shows that are more recent.

Truthfully, even Carmichael influenced a lot. I love the fact that here’s a show tackling really hard topics like consent but they’re doing it in a multicam format. Shows like that, shows like our show – that format still has a lot of life left in it.

I’m glad you mentioned Carmichael because that was definitely one of my favorite shows of the past decade.

Riddle: There you go. Great show. And so many friends are still on that show. It’s weird when I look at certain shows like Carmichael and Insecure and I think “Oh yeah. I worked with that person and I worked with that actor and I’ve been on staff with that writer and I hired that writer.” In my producing capacity between those two shows, if a bomb went off, I’d have to make new friends because there are so many people between those two shows that are truly great and killing it and having fantastic 2017’s. Despite everything going on in the world that makes me depressed and makes me never want to watch the news again, there’s some good stuff being made – some good creative stuff. And I hope we get to be a part of the discussion.

All that said, I think that Carmichael and Marlon are two entirely different shows. I think they reflect the personalities of the star of the show. And I think that’s okay because I don’t think the star of every show needs to be the same because it has black characters. I give NBC props for not putting the shows on back to back. I feel like that’s what would’ve happened in the 1990’s. The network would’ve had two black shows ostensibly about families. “Okay, those are clearly back to back so we can keep the blacks out there for an hour.” I don’t think that would’ve served either show, to compare them. I think they’re very different and they’re trying to achieve different things.

It’s amazing both Marlon [Wayans] and Jerrod get to express themselves in these shows, like you said, [that] are different. I’m so glad they exist because, five years ago, these things wouldn’t have been around. Insecure wouldn’t be a thing, Atlanta wouldn’t be a thing. None of these shows would be alive at all. It’s amazing that they can have all of these different conversations and be incredibly relevant for the next 45,000 years.

Riddle: 100%. I’m living proof of that because Bashir – my writing partner -- and I actually sold a show to HBO in 2011 while we were still writers at Jimmy Fallon. At the time, there was not one half hour black anything that I can think of that had the attitude and the tone that we were striving for. We actually ended up shooting two pilots with them – one called The Reporters and the other called Brothers in Atlanta. I stand by both of those pilots. I thought they were both super strong. They both, obviously, if they had been made would’ve come out before the current crop of Atlanta and Insecure.

I think the heart breaking thing and yet the encouraging thing about it is that after four years and two months of development, we have no show to show for it. But I think if either of those pilots were in development today, there’d be at least a 50/50 chance that they’d make it to air. I do think we’re 100% of a different environment than we were in 2011 when we first made our HBO deal and everybody looked at us like we were crazy because we wanted to do something that was – I will say – like a heightened reality. A heightened reality set in my home town of Atlanta.

We had to fight a lot of fights and we actually got a series order but it was rescinded when there was a little bit of an executive shuffle at HBO. I say all that just to say that I don’t think in 2017 you have to have as many conference calls, as many creative back and forths, and as many – quite honestly – fights to get something of their quality on the air. Right now, there’s a great opportunity for young creators to get their material on the air.

I live here in Atlanta and you would’ve had an easy time.

Riddle: What high school?

I went to Roswell High School.

Riddle: Roswell?

Yes sir.

Riddle: I know Roswell! I went to Mays High School…Mays High Raider and proud of it!

You would’ve had an easy time making that show here because Atlanta loves shows about it. Baby Driver is still being talked about; Atlanta won’t shut up about Atlanta. It’s crazy.

Riddle: I worked on Baby Driver. I helped out with the music. You can look at the credit sequence because I got a “Thanks” from the director. It says “Thanks to Diallo Riddle.” I would’ve even gotten a music supervisor credit but…it’s a long story. Basically though, when Edgar [Wright] was looking to, as he put it, “put a little Atlanta stank on it…” we have the same agent and they were like “Oh you should sit down with Diallo.”

We spent hours and days and weeks talking about music. Edgar’s one of my favorite filmmakers. I’ve been a fan since Shaun of the Dead. So the chance to work with him on that stuff…He already had an idea – I’d say of 90% of the music going in [laughs]. The fact I got to help out at all really makes me happy.

You talk about content being around for 4,000 years, I feel that way about my involvement with Baby Driver. When I finally saw it out here at the LA premiere, I was like “Holy shit! I got to be a part of something cool!” I could’ve been in this movie! He actually offered me a chance to do a cameo and, of course, I was out here shooting the HBO thing. Sometimes you make the wrong choice. [laughs]

That gig kind of goes in with what you do on the side. You’re a DJ whereas most writers are usually standups. You’re so good that you have residencies at six different places!

Riddle: My current exciting ones are Beauty & Essex, which is here as a part of the dream hotel complex. It’s like mini Vegas here in LA. The other one is Skybar which is in the Mondrian Hotel. Both are very cool for different reasons. Beauty & Ethics is white hot right now, as the expression is. And Skybar is a symbol of a place where it’s never going to go completely out. It’s always going to have a cool crowd. More importantly, that’s the place I can really let my freak flag fly. That’s the place where I can spin really any kind of music that I want. I can play that dude Lil Uzi Vert. I can also play underground super soulful house songs nobody’s heard yet except for a couple of underground U.K. cats. I can spin some weird soul funk that one of my other DJ friends put me onto. I really like having both venues because I get to explore the full range of music that I’m into.

Actually, that full range of music is going to be the basis of a pilot that we’re shooting for IFC, which got announced in the trades this week. It’s called Sherman’s Showcase. It takes place on the set of a fictional show very similar to Soul Train. Much like Soul Train, it’s been on the air for 40 years. Every episode of the show is a different year in that show’s history. We change the hairstyles; we change the clothing; most importantly, we change the music that was played on the show. It gives me and my writing partner, Bashir, a chance to write 40 years worth of original music. Whatever works. I love music. I love comedy. I feel like the two go extremely well together.

Since you have that IFC show and you have that Comedy Central pilot you’re also developing.

Riddle: Yeah! Comedy Central I’m really excited about. I was born in Atlanta. My writing partner was born in Chicago. The president just said he’s going to send in the national guard into Chicago. We just wanted to show there are people who live on the south side of Chicago and the majority of them are just like everybody else. They just want to laugh. They want to have good times. They’re aspirational. They want to get somewhere in life.

It’s very subtle but we show, in some ways, all the ways that the system prevents them from reaching their full potential all in a half hour comedy that will hopefully play for people who just finished watching an episode of South Park.

We’re getting ready to turn in that pilot as well as the IFC pilot in the fall. Hopefully, I’ll have Marlon where I’m acting and these two other shows where I’m writing. That’s what gets me excited. I like flexing one muscle over here, one muscle over there. I think it helps when you can be a member of all the guilds. Maybe one day I’ll try to direct. Right now, I’m pretty happy just acting and writing.

I’ll be there watching as you try to direct. I’m sure it’ll be as funny as everything else you’ve done.

Riddle: Thank you, man. I have the idea. I’m going to flesh it out over the next year. I don’t want to rush it. I think at some point – Heaven permitting – I will get to work on that. As writers, we worked on Jordan Peele’s upcoming show with Tracy Morgan. Those are two people we’d always wanted to work with. Before Get Out, we wanted to work with Jordan. And [we] had a really good lunch with him. He talked about his approach to directing and his approach to material that he thinks he might want to direct. I feel like I got some jewels out of that conversation. I’m going to keep them to the chest, see if they work. If they do, I’ll write a book and expose the truths about a very effective approach to directing for all those aspirational directors.

Since you wrote on the show, did you get to meet up with Tracy at any point?

Riddle: Absolutely. We actually met Tracy while we were working at Fallon. Tracy was on Fallon quite a bit. He knew who we were but we were still surprised when they called and said “Tracy wants you to come on and work on this show for TBS.” I’d heard the show was going to be kind of serious. When I met Tracy, in this context, he was like “Look, I want to do the show that people laugh one second and they cry the next.” It’s not a straight up comedy, it’s real life. In real life, you aint always laughing all the time and, in real life, you aint always crying all the time. There’s a lot of moments where you’re doing both. He was like “And that’s the goal of the show. So I want to tackle some serious subjects.” And we were like “That sounds like some challenging material. That’s all we really have time to do. We don’t want to do anything traditional.” So we signed up for that.

I think that show is really going to surprise people. The cast is ridiculous. You’ve got Tracy Morgan, Tiffany Haddish, Cedric the Entertainer. You’ve got this really funny LA improv comedian who a lot of people have seen in commercials, he’s done a lot of commercials – a white guy named Ryan Gaul.

Fun fact: me and Ryan were in the same Groundlings class when we first got to town. We didn’t know each other but I always thought he was funny. When we were viewing audition reels and we were looking at some pretty well known actors, all of the sudden Ryan popped up and he was just as funny as I remembered him all those years ago. This is probably like 2008. It was right before Chocolate News.

I said “You guys should really hire Ryan. I’ve been in that class with him. He’s always been funny.” I’ve always seen him in commercials and thought “How did Ryan end up doing commercials? He should be doing…he should be a movie star!” He’s so naturally funny and he doesn’t make the obvious choices. He got the job! I don’t even know if he knows all that so there’s your scoop! [laughs]

You gotta check him out on Bajillion Dollar Propertie$. That show is so funny.

Riddle: It’s so funny! So you know him?

Yeah!

Riddle: We had actors who’ve done movies coming in for the part he came in for. I was like “You’ve got to watch Ryan.” He’s great on Propertie$. I’ve literally always wondered “Why not more stuff for Ryan?” I feel like I did my job and now he’s actually going to be on a proper [show].

It’s on Seeso which just got ended today.

Riddle: Which is sad because I love the executives of Seeso. I thought they were all super dope. They had good taste. I just think whenever you put your stuff behind the paywall, that always makes it a little bit dicey. I loved him on that show. I’m happy that he’s now on TBS so nobody has to pay to see Ryan Gaul do his thing. I’m glad you’re a fan though! I’m glad you like him too.

I have to. I’m way too deep into this comedy world to not like anybody.

Riddle:…I’m one of those people that enjoyed @midnight. I didn’t watch it every night but I definitely watched it plenty of nights. I was so hurt when my publicist called and said “Hey, we’re going to do an episode with you, Marlon and Bresha Webb.” I was like “Finally! I get to be on @midnight! It’s going to be great.”

I’m friends with Ashley, Morgan Murphy, Ron Funches. I pulled together my dream team of writers. “I’ll be ready for anything!” And then of course Hardwick cancels the show. It was not meant to be. I was never meant to be on @midnight! Literally every single friend of mine…Sara Schaefer…has been on that show. Except for me. I will never be able to claim that.

[laughs]

Riddle: There you go. I’m bitter as fuck!

[laughs] I’m so sorry, Diallo. I’m so sorry!

Riddle: I was robbed, man. I was fucking robbed!

Don’t worry. You’ve got so many shows in development, so many other projects. You’re turning into Black Chris Hardwick.

Riddle: [laughs] I wish! What’s the Black Wall I wonder.

[both laugh]

Riddle: It’s probably just a college admissions or something.

[both laugh]

Riddle: What’s The Wall we gotta get over?

Affirmative action! That’s all we get.

Riddle: You get a seat at the college table and you get home safely that night. And you’re in The Wall! Unless the plinko chip sends you into a sub-prime loan debt or something like that.

[After a brief detour]

I’m excited for sitcoms to return to television with live audiences. That’s what most gets me excited.

Riddle: There’s no laugh track on this show. I will say, hopefully we get a second season. Because I think a second season....there were moments where the audience was ecstatic. Euphoric. Again, I haven’t seen these episodes yet. I’m hoping some of those takes are in there even if they run a bit long because what that live studio audience was feeling can at all translate through the TV screen, it’s going to be infectious and people are going to love it.

Follow Diallo Riddle on Twitter, heart him on Instagram.