It was never Chris Redd’s dream to be on Saturday Night Live. And yet the rapper-turned-comedian seemed to just be hitting his stride on the show when it was abruptly announced less than two weeks before the Season 48 premiere that he was leaving the cast.
In this episode of The Last Laugh podcast, Redd unpacks the mysterious circumstances surrounding his departure and talks about grabbing the spotlight for himself in his new HBO Max stand-up special Why Am I Like This? He also shares the gory details about the attack outside of the Comedy Cellar in New York that recently landed him in the hospital and weighs in on the controversy surrounding Kanye West, whom he memorably portrayed on SNL and who was, apparently, not a fan of his impression.
In any given week during his five seasons at SNL, Redd might get five, maybe 10 minutes of screen time. And aside from a couple of “Weekend Update” pieces, he was almost always in character as an unhinged celebrity like Kanye, New York City Mayor Eric Adams, or a mid-Oscars Will Smith.
So when it came time to finally introduce his real self to the world in his first hour-long stand-up special on HBO Max, Redd decided to leave it all on the table. For him, that meant everything from outrageous recreations of his childhood antics to frank details about his mental health struggles as an adult.
“It’s a combination of all the years of comedy, all the years being on the road. It’s really introducing people to me and where I’m at currently in this stage. I’m doing a lot of self-discovery and I’m really aggressive about my mental health journey and how it affected things,” he says, adding that the special is a “great way for people to see everything stripped down, not with a wig on or whatever—it’s just, like, me.”
For Redd, the biggest “challenge” of SNL was “trying to get your voice in there as much as possible and write something that’s as close to what you would naturally do outside of the show.” But after years of his sketches not making the cut, he says it was nice to know that couldn’t happen with Why Am I Like This?. “Even if I had to cut material. I’m still in it,” he jokes. “No one can cut me out of this shit. Ain’t no ‘cut for time’ here, baby!”
Below is an edited excerpt from our conversation. You can listen to the whole thing by subscribing to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Tuesday.
I love the part in your special where you’re talking about how SNL was never your dream and that it’s sort of a white person’s dream. I felt very seen when you joke about how much white people are obsessed with that show. So that really was never your dream, huh?
No, and I love that joke because it’s so true in a lot of ways. It is dream work and I did have a lot of fun. But nah, man, I’m not going to sit here and be like [it was my dream]—because I feel like it takes away from the people who were really dreaming about this when they were kids, you know what I’m saying? And I really wanted the gig a lot, especially when they showed interest, when they offered me the job, I was like, “Hell yeah, I want that.” But if I had never got it, I wouldn’t be down about that. I had already prepared in my mind that I wasn’t going to be on that show. And honestly, people just love the show, like so much, in a way where I’m like, “Man, you love it way more than me!”
Did you audition two years in a row? Because I remember something happened where you got falsely announced as being hired when you weren’t.
Yeah, man, this idiot blogger said I got the job right after I auditioned. And I was on a plane with the two other people—Melissa [Villaseñor], who actually got hired, but she wasn’t in that announcement with us. So I’m sitting here thinking she ain’t get the job, I got the job, and we’ve got to fly back together acting like we don’t know what's going on. Meanwhile she got the gig the whole time.
So then you found out that you didn’t actually get it. Was that tough to take, the roller coaster of that?
Yeah, because it feels so public, man. Like, I don’t really like my private life in the public, even though that’s kind of just happening right now. So it’s just weird, man, because if you don’t get a job at McDonald’s, you can just never go to that McDonald’s again. But when you don’t get a job like this, everybody’s checking up to see if you got it, if you don’t got it, why you don’t got it. It’s hard to move on. So that was happening for like three months straight. They were like, “We don’t see you in the credits!” I’m like, “I’m not on the show!” It sucked, but I just kept pushing. And then they called me back that next year and I was bitter as hell, but I still went to the audition.
Did you consider saying “fuck you” and walking away?
Oh, absolutely! But then, at the end of the day, I was thinking about the big picture of things, and I was like, let me just go do the audition. And they just brought me in for the callback. They didn’t make me go through the whole thing again. If I had to do the whole thing again, I don’t think I would have done it. But I went to the callback, had fun, and then they offered that to me that year, and I was mad excited.
What are your memories from that first week there? Because I feel like that’s always kind of an insane experience for people to walk into that show as something that you’ve only heard about or seen from afar. And all of a sudden you’re in it.
Well, it was hell for me, because when I got to the job that first week I didn’t know I was going to keep the job. I was in between contracts with Chuck Lorre at Disjointed and Lorne [Michaels] at SNL. And they were fighting to a point where I didn’t know if I was going to keep the job. So my first two months I was just on edge all the time, like, damn, am I going to be gone next week? So I couldn’t really get comfortable.
Lorne has a lot of power. And I guess Chuck Lorre has a lot of power, too, but I think Lorne might trump him.
Hey man, it’s two white men with money!
Fighting over you.
Yeah, and I love those dudes, shout-out to both of them, man. They ended up working it out, but that was my first time in a situation like that. And I was mad nervous. So that first six months was a blur, bro, but then I started getting comfortable after that.
One big breakthrough moment for you on that show was playing Kanye West opposite Alec Baldwin’s Trump at the beginning of your second season. I have to think that if you were still there, you would be all over that, because he’s the biggest story in the news right now. Is it hard at all to not be there and have that going on, thinking, “I would be crushing on the show right now?”
I mean, yeah, you know, I’m working on some things so that I can have an outlet in that way again. But yeah, of course I miss that outlet. And granted, I could write and just do something on my Instagram, but it’s different. It’s different than being on the show. But at the same time, I have other things I want to do. And I did a lot of that. But I will miss that. And Eric Adams. I miss doing that, too. So there are things about that show I will definitely miss, but I am really excited to just get back to stand-up and get to these other projects I’m doing. And figuring out my own platform to tackle some of these things that I got from the show.
Is it true that Kanye was not a fan of your impression?
I mean, it’s safe to assume my man don’t like that impression. Judging by interactions, I don’t think he likes it that much. But, you know, I don’t like what he be saying all the time. So I think we’re even there.
I think it was the episode before that one where you played him, he was the musical guest, and he did that crazy pro-Trump rant after he performed that didn’t actually air, but I think a lot of people in the room saw it. What do you remember from that?
I remember the dress rehearsal where he tried his dress rehearsal version of that, and I heard it, but there was music playing still so people were like sitting there and vibing. But I was listening to his words, and I was like, bro, he’s about to pull some bullshit. And I’m not about to be on stage for that. I’m not going to entertain this. Like, I’ve been a fan of Kanye my whole life. And I miss the old Kanye.
I think we all do.
But he came in there wanting to shoot everybody—verbally—and I just felt that was disrespectful, because we’re all grown adults. And now all of us don’t like you. He just came in there with a chip on his shoulder, ready to talk shit.
You mentioned the Eric Adams impression, which was another huge moment for you in your last season. And he actually told you that he liked the portrayal?
Yeah, he loves the impression, man. Me and Eric are real cool, so that’s my boy. And I always like when people can just not take themselves too seriously. He’s just a confident person, and confident people can take a joke, and that’s how it has always been. So in that regard, I really rock with Eric a lot. I want to see what he does with the stuff he’s supposed to be doing with the job, but on a human level he’s a dope dude.
I felt like with that impression especially, you were really hitting your stride on the show. So I was pretty surprised when it was announced that you weren’t coming back. And you were the last of eight cast members to leave, and I think some of that late timing led to speculation about whether you were leaving on your own accord or how that all went down. So was it your decision to leave the show, or how did that all play out?
Yeah, I left. I was trying to figure out when I was gonna go. And it was either going to be after this season or [before] this season. So, you know, a lot of things happened this year. I lost my friends this year. And there’s a lot of things I just want to do and have some of my life back and do some other things and comedy and create in some other ways, in other spaces. So I thought that it was better for my growth to do that. These projects will reveal themselves soon and I think it’ll make a lot more sense to a lot of people why I left. But that’s all I’ll say for now.
Yeah, and I don’t want to pry into your personal life. As you said, you like to keep that stuff private. But I’m sure you’re aware that there were tabloid rumors around your relationship [with SNL castmate Kenan Thompson’s ex-wife], that that had something to do with you leaving, and I just wanted to give you the opportunity to clear anything up around that. Did that play into your decision at all?
Uh, nah, but when it comes to all of that, I will speak on it. I’m not going to speak on it now, just because there are kids involved in all of this shit. And there’s just a lot to it. But I will say there’s more to it than people know. So until I’m ready to talk about the whole thing, I’m just not going to say too much more about that shit. But those two things ain’t really related like that.
You said you have other projects in the hopper, maybe things you can’t talk about yet. What are you trying to do next that you couldn’t do when you were at SNL? I know it can be limiting in terms of what you’re able to do outside of that show. What are you excited to do now that wasn’t really an option then?
I’m really excited to write a show, to write a single-camera show. I’m really excited to get into the horror-comedy space. I’m really excited to keep pounding the pavement on stand-up, get my next special out. I’m really excited to get into some comedy music and do it no holds barred and work with my favorite artists, people who I wouldn’t have had the time to work with. So yeah, I have a few things up my sleeve, player.
Listen to the episode now and subscribe to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Tuesday.
