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Melissa Harris-Perry: We're back with The Takeaway. I'm Melissa Harris-Perry. Back in May, writer, actor, director, and comedian, Bashir Salahuddin stopped by The Tonight Show with Jimmy Fallon. Now the appearance was a bit of a reunion early in his career, but she had been a writer for Fallon, but he didn't return to the writer's room. He took a seat on the guest couch, fresh off his star turn, and the blockbuster hit Top Gun Maverick.

Speaker: Did you guys bond you and Tom Cruise?

Bashir Salahuddin: Oh man, he just texted me yesterday because we had a screening issue. I feel like I'm bragging, and it's not even, I'm just telling the--

Melissa Harris-Perry: Now this disarming little humble brag just might be a Bashir's specialty. As I quickly learned when I sat down with him earlier this week, a Harvard graduate who started off college as a pre-med major, I teasingly asked if he'd become a comedian after failing organic chemistry.

Bashir Salahuddin: As the old folks say a lie is all the way around the world [laughter]before the truth gets out of bed. No, organic chemistry was one of my best grades in pre-med actually.

Melissa Harris-Perry: Oh, okay. Slight class.

Bashir Salahuddin: Let's put it that up right now. Now your boy understands Valance. Let's get it going. No. The class I almost failed was college physics that kicked my butt.

Melissa Harris-Perry: Oh, I see. Organic chemistry was a breeze. It was just that Harvard physics that provided a challenge, well-played and revealing. As an accomplished comedy writer and showrunner there wasn't any doubt, Bashir was funny, but he just let me know he was smart and charming as well. Smart, funny and charming also describes Salahuddin's body of work. Along with comedy partner Diallo Riddle, his co-creator and co-star of Sherman's Showcase. It's a variety show with a 1970s citation vibe. Wholly familiar and genuinely original.

Speaker: Hello and welcome to Brother, You're Wrong.

Speaker: Hold up brother, you're wrong. Now this is my show and I should open the discussion.

Speaker: Brother, you're wrong. That's mad Territorial of you to be like, "This is my show." This is our show.

Speaker: Brother, you're wrong for assuming that I wasn't going to show Love to the Table. How that --

Melissa Harris-Perry: Then there's his HBO sitcom South Side, set in his hometown, Chicago.

Speaker: Take him out, if the word shady was in the dictionary, this dude's picture would be next to it.

Speaker: Shady is in the dictionary. Have the people who shop here shady. I just helped the guy wearing jeans on top of jeans. Get some office chairs.

Speaker: Oh, damn that's Fred. He's doing that Jean on Jean again. Let go [laughter]

Melissa Harris-Perry: South Side delivers, as one member of team Takeaway described it, rib-breaking laughs. It isn't just hilarious, it's accurate. Propelled by an affectionate authenticity derived from growing up on the south side. Bashir truly sees, hears, and feels the people who are characters in the show, but the comedic cultural gifts that our Sherman's Showcase in South Side almost never came into being. After all, Bashir is a smart kid from a striving working-class Black family.

Bashir Salahuddin: I do feel like the fact that I was able to get into Harvard it's important how you utilize such a great opportunity, and then certainly going into the arts was really not on the list of accepted inner city kid careers who got in Harvard. Eventually, I had to call my dad and say, "Look I don't think I'm a doctor. I think I want to play a doctor." Definitely, he is like, "If you get a chance to go to a school like that, are you going to go into the arts?" Which is very, very, I would say almost a higher than zero, but a very low guarantee of being able to actually do better than your parents did.

I think in our community, personal fulfillment feels like the more you seek it, especially if you aren't really taking care of yourself and your people, then you are being selfish, and you are really not building on all the work that the people before you had to do. You could even have an opportunity to go to a school like that. As an artist, it's tough, and I'll say that, that even goes beyond race.

It even goes beyond economic status. No matter who you are, if you choose to go into the arts, there is that moment of like, "You understand this could all just fail." It could all come crashing down. It's not easy. There's a lot of rejection, but for me, there were two reasons that I ended up having to stay true to it and having to have this revelation with my parents. The beautiful thing was, again, my dad said at the time, he was like, "I think we always knew you were an actor, and so this is not really surprising."

I was like, "Okay, good. I'm glad I was communicating that." I do feel like I looked up, and I was like, "Man, you're calling yourself pre-med, but all you do with all your free time is theater. You can't do enough theater or spoken word plays or whatever." I was writing plays undergraduate. I was reading other people's work. I was so immersed in it and I'm very fortunate that at least being from where I'm from, I did have a certain modicum of toughness. I was ready to take that journey and I knew the journey was not going to be easy, but I do think it worked out.

Melissa Harris-Perry: I love, as you were telling that story, there were all these other parts that I kept hearing. There's a generational piece, you got a little bit of that kind of Gen X notion of like, "Yes, it matters what you love, but also you owe something to folks."

Bashir Salahuddin: You do. For real, yes.

Melissa Harris-Perry: There's also a lot of that first-gen immigrant kids story there. You are real Chicago in so many ways, and your dad is from Panama.

Bashir Salahuddin: He's from Panama.

[laughter]

They all came to Chicago when he was like, I don't know how old he was. Because here's the problem with some of our oral history. It's real inconsistent from relative to relative, and this is the true thing about Black people. They were over there in Panama not making it, and of course, there was always that journey. We had to have a better life. We got to do right by these kids, and my granddad had six kids, and so he came over first, and then he labored and labored, and then he had enough money and enough whatever to finally get my grandmother and didn't really speak any English.

Then they went right to the South side of Chicago and the south side of Chicago got jokes. Here come these people with these weird accents speaking this weird language, and they had to get their lumps in, but to their credit, they figured it out, and they really did become Chicagoans. I've begun really trying to embrace that side of my history. When I was growing up in Chicago, it wasn't until I went to college on the East Coast that I learned that, "Oh, there's not just Black people. There's Haitian and Bermudian, and Bahamian and Beijingian.

Melissa Harris-Perry: You're like, "We just Blacks." [laughs]

Bashir Salahuddin: Damn, Chicago is you Black. You black. Then it wasn't like I had friends, I was like, "What? You Haitian?" We were the high school for three years. I never knew that. He was like, "Yes, man." [laughs] It's not until you really get to these --, in some ways the East Coast schools where you have all these wonderful groups like the --, they have these Caribbean societies, and the West African Club and all this stuff.

That you really like to learn a little bit more about where the diaspora some of your folks came from. For me, again, in Chicago, it was like, "I was Black." Then after a while I began to realize, you know what, there's so much richness, not just genetically, but also culturally with regard to food and things, and what my dad would make for us growing up that I want to embrace, and I want to know more about it. I really began to explore Panama more as I got older.

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Melissa Harris-Perry: We're going to take a quick break, and we'll be right back with the humor and heart of Bashir Salahuddin in just a moment. It's The Takeaway. We're back and talking with writer, director, actor, and comedian Bashir Salahuddin. Now, it was supposed to be a conversation about his work, but let's get real. We spent most of our time talking about his hometown Chicago. Good thing that his wildly successful and much beloved HBO sitcom, South Side is also all about Chicago.

Bashir Salahuddin: South Side, is a half-hour comedy. It's based in and around the south side of Chicago, where I'm from. It comes from a lot of different places, but where it really primarily comes from is two places. It comes from both my brother Sultan having known that my writing partner and I were looking for a show to do that was based on one of our hometowns. My brother identified this place Rent-A-Center as potentially having been in a great location to do a show around. We went to this Rent-A-Center place where you rent furniture and appliances, and if you don't pay, they come get it from you.

It's really very pervasive in low-income communities, but it's also how low-income folks have TVs and video game systems that enjoy the stuff that they see other people doing. What we found is that because the store requires you as an employee to drive around the city, that it allowed for us to tell a story and have a TV show in which the characters were forced by virtue of their jobs to be in and around the city of Chicago. We thought that was quite beautiful, that we could not only do a show about some blue-collar folks, but also a show that really showed off the city and really got to know the south side.

That's one place it comes from. The other place it really comes from is me and my writing partner Diallo our desire to just do a really great comedy. Part of the reason we wanted to do that is because Chicago was so maligned. I would hear about my hometown in the news, and I'd be like, "I don't know what city they're talking about. Don't get it wrong, there's definitely challenges." The vast majority of folks, especially Black folk on the south side they're chill, they're funny. They got jokes. They're going to talk about you.

One of my buddies is want to say if you go in somebody's house on the South Side Thanksgiving, you going to come out family. Chicago people are very loving and they're really funny. That's another thing is that the South Side was really never given its props for the comedians like Robin Harris and the Dell Givens who's on the show this season, and all these really great and funny voices because Chicago comedy and we love the North Side, but so much of Chicago comedy was centered on your Highland Parks, your Ferris Bueler's, your breakfast clubs, your Blues Brothers.

These are things that are mostly downtown North Side things. Again, it was almost like, "Hey, it's not just the North Side that's funny." The whole city has so much to offer comedically, and it's such a much more comedy-forward place. I got to tell you when we shoot the show the people who pass on the street, everybody, they love it. They're happy. To a person, 100% of them are sure that the only thing our show is missing is them.

Melissa Harris-Perry: That's all right. [laughs]

Bashir Salahuddin: A lot of people, they'd be like, "Hey man, where you playing, bro? You know you got to get me in this scene, man, come on." We do that sometimes you'll actually see in the first episode of season three, there's a dude who was a snow cone vendor in my neighborhood, and I just went to buy snow cones one day and he made me laugh. He's on the show.

We're at a point now when we're shooting people yelling out of car windows. "Oh, they shoot South Side." It's like, there's a sense that we have been welcome. There's a sense that people like what we're doing and that means a lot.

Melissa Harris-Perry: Let's talk about Sherman's Showcase, which is your comedy, but is also real different than South Side. It also, again, you pointed at the generational Sherman Showcase feels more like, "Oh, I know what this is. I recognize this as a kid born in the '70s."

Bashir Salahuddin: For each of our projects, and I'm going to really give him credit. Either my writing partner or I will become the captain of that project. We found that we're a partnership, but at the end of the day, somebody has to steer the ship. For Sherman Showcase, that person is Diallo Riddle and he also plays Dutch on the show. We wanted to do a sketch comedy show.

We knew we wanted to do a sketch comedy show because that's how we got started. We got started in a sketch. We got started, and there was a sense of frustration that we weren't really doing what we wanted to do. We began to write for ourselves. We began to work together. We put together a sketch comedy troop called Cleo's Apartment.

That's actually how we ended up getting on Jimmy Fallon's radar. Ended up writing for him for four years. We wrote for them. Before his show started through the first four years we were part of that core writing team, but eventually, we knew we wanted to do our own sketch comedy show. As a writer, you go, look, I love to be able to help somebody else's vision. At some point, we want to create our own.

We realized we were doing some like doop sketch at one point with Jimmy and I think that's when we realized like, "Hey, this feels like what our show should be. This feels like the form." We picked a '70s variety show from that obviously Soul Train is a huge influence, but there's also American Bandstand, there's also Bert Sugarman's Midnight Special. There's all these other, like at some point in the '70s, everybody in their mama had a variety show.

They were just giving them out like hotcakes. We knew by doing a variety show that it allegedly or pretended to spend decades. It would allow us through comedy from the past, the present, and the future. Part of that again is the writers collectively having probably combined 40, 50 years in comedy. We're just like, how do we continue to both services the basic form, which is just doing a funny sketch comedy show but also service our experience, which says we're experienced enough that we can put a little more energy into this and figure out a truly unique comedy delivery system.

[laughs] The comedy delivery system was a variety show in which I play the host unhinged, completely inconsistent, [laughs] politically all over the map has no loyalty, is self-interested. I really based him a lot on Crusty the Clown. Like he's one of my favorite characters because it wasn't until I got to Hollywood that I was like, "Man, crusty is like the most accurate representation of Hollywood [laughs] in the world." All he cares about is the next day's ratings. I was like, that's literally how it is sometimes.

Melissa Harris-Perry: I think sometimes the question that gets asked is like, so what's your advice for young folks? I want to ask it slightly differently because of the framework you gave me of doing this work, having these extraordinary opportunities, doing this work in terms of making someone else's vision come true, and then ultimately moving into making your own vision real. Can you talk to the young creators out there whether they're in news production or whether they're in a comedy, but they're artists, they're writers, they're thinkers about that transition and about how to maybe think about those different parts of the long career?

Bashir Salahuddin: I think you just nailed it. I think you have to assume that you will have a long career. The reason I moved into mine was two parts. One part I had a passion for it, and the other part of it was that people loved when I did it and wanted more from me. Again, I have memories even before I solidified my sense of wanting to go into the arts of performing and getting plotted and ovations and what have you.

It wasn't like, I was like, Well, there's no evidence that I'm good at this. It was like, no, there's tons of empirical evidence that this is something you maybe should be doing, but everything is education. Everything has to be your education. I look at my failures as educational and one of our writers, for example, who wrote in our writer room on South Side is now writing in another room, but we were talking about it and they were like, "Yo, it sucks and this dude is mad terrible. I hate working for him." [laughs]

I was like, that's all part of your education. You got to have people you love working with, and you got to have some jobs where you're like, "This is terrible because then it's all part of your education and you learn." I always tell people that that's a very big part of a long career is knowing that everything you do is contributive to that. There's always this impetus to do your own thing, but you got to be okay working for other folks sometimes because there's so much to learn.

You won't get all this education if you don't go out and do stuff. That's why I'm always telling people to just make stuff. I'm always telling young artists and writers go make something. People would much rather watch a short film than read a script. I think also, and this is something I suffer from too, it definitely feels like you're on a clock, especially if you come from circumstances like mine where your family doesn't have a lot of money.

You do feel like, ah, this is taking too long and what's going on? I'm getting older. I'm looking at 30 right now. I'm almost 30, and I still haven't really made a penny doing this stuff. I probably didn't make any money writing until I was 29, 28, or maybe 30. It took a long time. There was many, many, many years of busting my ass and making nothing. All that stuff was contributed, all of it helped so that when it came time to seize my own opportunities, I was ready. I was like, "Yes, I know what to do now."

All those little pieces they add up and eventually it'll be obvious to you the best way to proceed to present your own work. Hopefully, this is actually really crucial, and I really got this from Paula Vogel. She's a writer. She wrote up the Baltimore Waltz and I was at the Hangar Theater, and she came up to do an artist day with us, and she just talked to us about being an artist.

She said the best advice she could give us was that circles rise together. What she meant by that was the best way for you to advance and do more is to reach out laterally to your peers, not up to people who are more advanced in their careers, who are going to somehow pull you up. It doesn't work like that. If you look at George Lucas and Steven Spielberg, these guys are all friends. They were all broke, they were all making movies together. The question I always ask is, who around you is as hungry as you are because that's who you need to be messing with?

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Melissa Harris-Perry: That was Bashir Salahuddin, actor and co-creator of South Side on HBO Max and Sherman's Showcase on IFC.

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