Oh my God, there it is.” Bashir Salahuddin is standing in front of his childhood home, a brick three-flat on Constance Avenue in South Shore. It’s been a minute since the actor, writer, and impresario behind not one but two hit comedy series has been back to this spot — 20 years, in fact — so the nostalgia is running deep. “My grandmother owned this entire building,” says Salahuddin, who now makes his home in Los Angeles. “She lived on the basement floor, rented out the first floor, and my family lived on the top.” His youngest brother (of his seven siblings) and a cousin still live there.

He walks to the side of the row house to size up a narrow gap, maybe three feet wide, between its porch pillar and the one of an adjacent building. Back in the day, when he was a boy who “nerded out” on comics and played Transformers in a weedy nearby park, just off 73rd and Stony Island, Salahuddin and his friends used to climb that gap Spider-Man-style, pressing against the two pillars, and vault onto the small ledge on the second floor.

But he is 43 now and not exactly in superhero shape. Still. “If my brother was home, I could try and do it,” he says. He feints a step forward, as if he’s going to go for it, then takes a step back, as if the reality of how it might all go down has suddenly dawned on him: a grown-ass man — six feet, 260 pounds — trying to gain purchase on a sheer vertical surface wearing fresh-out-of-the-box Nike Air Max 95s and black jeans riding low.

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Nah.

“As a kid it didn’t seem scary,” he says. “But you look at it now and that shit looks tall.”

He bends over in mock exhaustion.

If the nightly news is your sole source, the South Side might seem a breeding ground for misery. But when Salahuddin (pronounced sal-la-hoo-DEEN) walks these streets, he sees potential for comedy, from the weave shops and chicken shacks and rent-to-own stores and storefront churches to the mansions of Hyde Park and Jackson Park Highlands. Amid the daily grind and universal frustrations, humor is as much a part of life here as the rumble of a CTA bus. It’s all fodder for South Side, the lauded Comedy Central series Salahuddin cocreated, which was recently renewed for a second season.

Though the show is satirical (think Reno 911! or Canada’s Trailer Park Boys), authenticity still underscores it. All exterior shots are filmed in the city, showing real businesses and homes, from Chatham and Auburn Gresham to Englewood and, naturally, South Shore. Every one of the writers — with the exception of Diallo Riddle, Salahuddin’s friend, cast mate, and cocreator — has Chicago roots. The cast includes an amalgam of people Salahuddin knew from his childhood, such as twins Kareme and Quincy Young and Salahuddin’s older brother Sultan and younger sister Zuri. Even his mother, Renee, has appeared on the show. “We wanted two kinds of people in the cast,” says Salahuddin. “Hilarious actors who will give you something different on every take and it’s always going to be good, and people who may not be professional actors, but they’re just naturally fucking funny. We wanted people who could talk authentically about the city. We didn’t want to be carpetbaggers.”

The show draws heavily on his and the other writers’ experiences. In one episode, Officer Goodnight, the overly by-the-book policeman played by Salahuddin, tries to do a good deed for a father and son by letting them cut in line for the latest Air Jordans, only to realize the man actually has twins. “Oh shit, Sophie’s choice,” says Goodnight’s partner and foil, Sergeant Turner, played by Salahuddin’s wife, Chandra Russell. The scene was inspired by Salahuddin’s desperation as a youth in trying to score new Jordans.

Likewise, Goodnight’s backstory was drawn from an incident involving a professor Salahuddin met while attending Harvard. The running gag is that Goodnight had been on the cusp of being made a detective until he arrested a famous black academic trying to get into his own home. That, you might recall, actually happened to Henry Louis Gates.

South Side is riddled with Chicago-centric references. In one episode, a new employee at the rent-to-own center where much of the show takes place halts a morning meeting to introduce herself: “Yes, I went to Kenwood. Yes, I know Eddy Curry. We used to go together. Yes, I was at his first and last game. Yes, it was in the same year. Yes, I used to braid his hair. Yes, I have a son. He is an elite basketball player. Chicago Reader listed him in ‘15 to Watch Under 13, South of 22nd Street.’ ”

 
Bashir Salahuddin

Salahuddin is blowing into his hands. It’s a few minutes after his visit to his childhood home, and the Prodigal Son Returns tour continues with him swinging by the South Shore Cultural Center, the grand Mediterranean Revival building where Barack and Michelle Obama held their wedding reception. Salahuddin zips up his light jacket with an exaggerated shiver. “I made the classic Chicago mistake,” he says. That is, not packing a parka in the unpredictable fall. “Man, we might have to stop somewhere, get me a coat.”

Salahuddin’s face is onscreen a lot these days. In addition to South Side, he appears on the Soul Train–inspired IFC sketch show Sherman’s Showcase, which he and Riddle created, has a recurring part on the Netflix series GLOW, and played a police detective in the 2018 sleeper-hit movie A Simple Favor. Still, the security guard at the cultural center doesn’t recognize him. That could be because Salahuddin isn’t quite famous enough yet, or maybe it’s because he’s given his beard carte blanche to grow as it will until South Side’s filming begins again this spring.

Soon we are on to our next stop, walking through Rainbow Beach Park to the stretch of shore along Lake Michigan between 75th and 79th Streets. “We used to go all the time,” Salahuddin says, gazing out across the wide swath of white sand to the manmade limestone ledge that serves as a shorefront promenade. As with the cultural center, where blacks were once prohibited, the beach has a fraught racial history, at one point serving as a de facto whites-only spot. Both integrated only after white flight changed the makeup of the neighborhood. Salahuddin knows all about this, and his show, even as a comedy, doesn’t ignore the issues that are a part of the area’s past and present.

In fact, an interesting wrinkle in the Goodnight character is that, in addition to being a lovable buffoon, he despises the South Side. In one scene, his partner arrives at the house of Zuri Salahuddin’s character, Stacy, to get her hair done, and says, “I love this neighborhood. It brings back memories.”

“What’s there to love?” Goodnight responds. “I see several robustly empty lots, big-ass dumpster right there.”

“This is the historic South Shore,” Stacy claps back before treating him to a non sequitur burn. “You know what? You can’t even come in my house, looking and smelling like Gerald Levert.”

There’s a reason Salahuddin included a character who feels the way Goodnight does. “I wanted to use him to live the criticism that people read about when they read about Chicago — that this place is bad, it’s violent, or whatever negative things there are. I think he’s that op-ed.” And through his characters responding to Goodnight, Salahuddin can respond to the criticism. Even if it comes in the form of one-liners.

 
With Russell at the Screen Actors Guild Awards last January; with his father, Ismail, and two of his seven siblings; with South Side cocreator Diallo Riddle last June on ‘The Tonight Show Starring Jimmy Fallon’
Clockwise from top left: With Russell at the Screen Actors Guild Awards last January; with his father, Ismail, and two of his seven siblings (Salahuddin is at left, and Sultan, who now has a role on South Side, is at right); with South Side cocreator Diallo Riddle last June on The Tonight Show Starring Jimmy Fallon, where they were staff writers for nearly four years. Photos: (SAG) Steve Granitz/WireImage/Getty Images; (with father) Courtesy of Raja Salahuddin; (Fallon) Andrew Lipovsky/NBC

Bashir was always funny,” says Sultan Salahuddin, who plays the get-rich-quick-scheming underachiever Simon on the show. In the Salahuddin family, you had to be. “Man, that living room was like Amateur Night at the Apollo,” Sultan recalls. “The jokes would be flying from corner to corner, and you’d not only have to be able to give it out, you’d have to take it, because as soon as you said a joke, somebody would come back at you quicker and hotter and funnier.”

Bashir was smart, too. Yes, he enjoyed playing basketball and softball in the streets, even when the games would get called off because of a pack of menacing dogs. (“That was a thing,” he says.) But he also loved astronomy and art and just about any other bookworm endeavor that would light up his imagination. Recalls Sultan: “I would go out and play at like 1. I’d come back at like maybe 6 after doing my thing, and he would still be in the same spot reading books.”

Salahuddin credits his parents for nurturing his curiosity. “They knew how to throw gasoline on our educational interests. On the weekends, they would take us to the Museum of Science and Industry or we’d go to the DuSable Museum.” His mother taught elementary school in Hyde Park. His father, an immigrant from Panama, spent much of his career as a mechanic for the now-defunct Midway Airlines before winding up as a teacher, too. (Later, after Salahuddin left home, they divorced.)

Salahuddin tested into Whitney Young, a selective enrollment high school. There he excelled, becoming president of the school’s chapter of the National Honor Society. He also got a chance to perform in front of an audience for the first time, acting in plays such as The King and I, Cyrano de Bergerac, and Les Misérables. “I was aware that I felt super excited and comfortable onstage,” he says. The highlight came his senior year, when he was cast as the evil stepfather King Claudius in Hamlet. “I got to get killed onstage every night. Shit was badass.”

He entered Harvard as a premed student — not because he had a burning desire to practice medicine, but because it seemed the right thing to do. “You come to Harvard from the hood and you’re either going to be a doctor or a lawyer, you know?” But he struggled as a freshman. “I just wasn’t interested in it. I didn’t want to go to labs, I didn’t want to go to any of my premed classes.”

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Toward the end of his first year, he met a student who felt similarly adrift. Like Salahuddin, Diallo Riddle had come from a working-class background and was raised in a big city — in his case, Atlanta. And like Salahuddin, he loved theater and music. But the idea of making a career of those interests had never crossed their minds. The two spent their free time singing for change in Kenmore Square and Boston Public Market and “cracking up people at the cafeteria lunch table,” Salahuddin says.

Had they known the direction they’d ultimately choose, they might have written for the Harvard Lampoon. “It famously has this nice little built-in infrastructure where it can help you get a job in Hollywood,” says Salahuddin. Instead, he hung out with his new buddy, “completely eschewing and misunderstanding the whole point of going to a school like that, which is to make fancy connections. We were just like, ‘Ah, here are some other broke people. Let’s hang out with each other.’ My parents were like, ‘You ain’t got no rich friends here? What the hell?’ ”

When he returned to Chicago that summer, he had a revelation. He had accepted an offer from a couple of Jackson Park Hospital doctors to shadow them as an unofficial intern. “One of them brought me right into the damn OR. He’s like, ‘Come on, man. You’re going to see the shit today.’ Literally I saw a prostatectomy, the whole nine. I was like, This is wild, but it’s not who I am. I had that moment of, What the hell am I doing?”

He soon found his true calling: drama. His sophomore year, he auditioned for a Harvard production of Othello and “crushed it,” landing a part. He was nervous about telling his parents about his change of plans, but they were supportive, to the point that his father paid for him to attend the Hangar Theatre’s training program in upstate New York one summer. “For the first time, I really just studied acting, and it was wonderful,” Salahuddin recalls.

After graduating from Harvard in 1998, he returned to Chicago, where he did paralegal work to save up enough to join Riddle, who had already moved to Los Angeles. Finally, with $3,000 in his account and no real plan, Salahuddin headed to Hollywood. Soon both young men landed jobs as production assistants: Salahuddin at Warner Bros., Riddle at Paramount Pictures. “Over the next year and a half, I just committed myself to learning the business,” Salahuddin says. When he left Warner Bros., he told himself, “I’m not coming back here until I can come back as an actor.”

Salahuddin at the Harold’s Chicken Shack on 63rd Street, filming a scene for ‘South Side’; As Officer Goodnight, with his wife, Chandra Russell, as Sergeant Turner
Salahuddin at the Harold’s Chicken Shack on 63rd Street, filming a scene for South Side, the Comedy Central series he cocreated. Lower photo: As South Side’s Officer Goodnight, with his wife, Chandra Russell, as Sergeant Turner. Photos: (on set) Antonio Perez/Chicago Tribune; (South Side) Courtesy of Comedy Central

For the next few years, he “just hustled,” he says. “I worked a ton of odd jobs, every small job you can think of.” He landed a few acting gigs — mostly commercials, a couple of spots on TV shows. Then he discovered Sacred Fools. On Saturday nights, the Los Angeles theater hosted Crime Scene, where writers performed comedy sketches. “The first time I got out there, I was in a little goofy costume and I got some huge laughs, and I was like, Oh shit, this is what I need to be doing. Not just regular acting — which I love — but comedy stuff.”

Still, he struggled to get a foothold in the business, continuing to grind away at temp jobs while performing sketches on the side, mostly for no pay. Salahuddin began to doubt himself. By this time, he was doing so much substitute teaching that when people asked what he did for a living, he began to cite that instead of acting. By the mid-2000s, he had fallen into a deep depression. “I’m like 26, 27, staring down the barrel of 30, and things just weren’t going the way I wanted them to.”

Then, in 2007, came the break he’d been waiting for. Salahuddin and Riddle had been creating sketch videos and posting them on YouTube. One of them, “Condi Rice Raps,” blew up. In its first two days, it got 2 million views. CNN even posted a story about it.

In short order, the two had a major agency calling and were brought on as writers for Chocolate News, David Alan Grier’s satirical news show on Comedy Central; when that folded, they found themselves sitting in Jimmy Fallon’s office, successfully interviewing for jobs on The Tonight Show. Soon they were coming up with such classic recurring bits as “Slow Jam the News,” in which celebrities (including Barack Obama) read an update over a groove while Fallon purrs sultry echoes.

“We learned so much about professionalism,” Salahuddin says of their stint working on the show. “We learned about endurance, because you got to make comedy every day. Nobody cares about how good yesterday’s show was.” It was also at The Tonight Show that Salahuddin met his wife, when she auditioned for a role as a dancer in a Soul Train send-up sketch.

After nearly four years with the show, Salahuddin and Riddle left in 2011, when HBO greenlighted an idea they’d pitched for a series. The concept was similar to what would become South Side, but it was set in Atlanta, Riddle’s hometown. After years of false starts, though, HBO execs eventually cooled to the concept and, in 2016, finally pulled the plug. A payout from the network did little to lessen the heartbreak, but it did buy Salahuddin and Riddle some time to regroup and plot their next move.

They began thinking about the stories that Quincy Young, one of the twins Salahuddin had grown up with, told them about his time working at a rent-to-own furniture business. “Bashir thought that was a funny idea for a show,” Riddle recalls. “He’s like, ‘Let’s do this big, with my brother and my friends, these two twins from Chicago, and let’s make it, like, you know, Trailer Park Boys.’ ”

They pitched the concept to Comedy Central, but instead of sticking with the traditional route of submitting a script, they also created a “sizzle reel,” a short video that offered a feel for what they had in mind. The network loved what it saw, and so did viewers: More than 2 million tuned in to South Side’s debut in July. The show has earned raves from critics — a 100 percent rating on Rotten Tomatoes.

The creators can count at least one celebrity fan, too. Salahuddin was cast in the Top Gun sequel due out this summer. While on the set, he was looking at some South Side clips when Tom Cruise happened by. “He loved it,” Salahuddin says. “He was literally going through every single episode.” Later, when Salahuddin was back in the writers’ room for South Side, Cruise called, and Salahuddin asked if he could put him on speaker. “He was like, ‘Yes, put me on.’ I said, ‘Hey, guys, Tom Cruise wants to tell you how much he likes the show.’ They were like, ‘What the fuck are you talking about?’ ”

It’s just one of the ways things have changed for Salahuddin these days.

“For the first time in my life, I’ve been getting acting parts without having to audition,” he says. “I’m like, Oh shit, this is nice. Hello.”

 
Bashir Salahuddin
The return of the prodigal son: Salahuddin snaps shots of his South Shore childhood home on his first time seeing it in 20 years.

Rainbow Beach is the last stop on Salahuddin’s impromptu tour of the South Side. He needs to head back north to his hotel. He’s giving a talk later for Chicago Ideas Week. In two weeks, he’ll be back in town for an Obama Foundation summit.

Not far from the park is a high-rise where, in one episode of South Side, Goodnight gets trapped on the roof after chasing a suspect. His partner offers to send a helicopter. But, she adds, “then you’ll be known as Helicopter Guy.”

“No, don’t do that,” Goodnight responds. “I’m already the Guy Who Broke the Keurig. I can’t handle another title.”

Hours pass, and night begins to fall across the South Side that Goodnight despises. He grows contemplative and begins to sing:

Stuck on the South Side.
Nowhere to go.
Who will come save me?
I don’t knowwwwwwww.

The songs begins to crescendo:

I’m stuck on the South Side.
Hey, take your best shot!

Now it explodes into a full-blown, Broadway-style showstopper:

Am I stuck on the South Siiiiiiiide?
Or is the South Side stuck on …

There’s a pause for a quick tap-dance shuffle.

… meeeeeeeeeeeeee?!

The over-the-top hamminess is Bashir Salahuddin in his purest form. As for the underlying sentiment, his own experience puts a twist on it: Yes, you can leave the South Side, but you don’t have to leave it behind.