Want to Understand Chicago’s Stand-Up Scene? Michael Alexander’s “Out of the Loop” is Mesmerizing Must-See Viewing

Michael Alexander’s new film about Chicago stand-up, Out of the Loop, is wall-to-wall “wow” moments. From the first minute, we’re flies on the wall in the lives of Chicago’s comedians. As the film opens, we hear a personal voicemail to Michael from Better Call Saul’s Bob Odenkirk (Berwyn native, student of Del Close, Second City alum). We’re privy to Odenkirk’s diplomatically stated reason for not participating in the film. It’s a real “Yes, and …” moment because Michael goes on to interview a veritable who’s who of Chicago stand-up royalty.

Just like on stage, these comedians offer up unflinching honesty and insight. We come to understand why Chicago occupies such a unique place in the stand-up world. The film covers the birth of Chicago as a stand-up epicenter in the 1980s through to present day. When the scene was still in its infancy, legends like Tom Dreesen, Marsha Warfield and Judy Tenuta were forced to create their own spaces. They reveal first-hand how they did it.

Godfrey, Rocky LaPorte and Kyle Kinane offer hilarious confessions about their first time doing stand-up. Jeff Garlin tosses around career highlights and lowlights that you won’t see in People.

In the early 2000s, Chicago became a place where you might see future stars like Lil Rel Howery, Chris Redd, Pete Holmes, Hannibal Buress, Kumail Nanjiani and TJ Miller all in one place in one night. They all (except for Nanjiani) appear in Out of the Loop, with straight talk about their early careers and Chicago’s role in their development. (Some of it was a fairy tale. Some of it was harrowing. All of it is eye-opening.)

I watched Out of the Loop on Amazon Prime three times, each time slowing it down more and more to savor every jaw-dropping revelation and rare video clip. Michael conceived the film as a celebration of Chicago stand-ups and their worldwide influence as performers, writers, directors and creators. Until now, too few people knew these details.

But to Michael’s surprise, the celebratory tone didn’t last. Cracks appeared in the happy narrative and the reality of racism, sexism and antisemitism busted through. Significant figures, including co-producer Dwayne Kennedy, Patti Vasquez, Deon Cole, Damon Williams, Anthony Griffith, Sonal Aggarwal, Azhar Usman, Kara Buller, Owen Smith,  Mary Lindsey, Raymond Lambert, Ali LeRoi, Erica Nicole Clark, Lance Crouther, Shay Shay, Chuck Sklar, Megan Gailey, Paul Gilmartin, Hannibal, Lil Rel and Chris – and more –   share insight and  personal experiences. Multiple club owners weigh in to present their side. Michael respects us viewers enough to let us come to our own conclusions.

This movie has so many highlights, it’s impossible to list them all. Just a few more: Dwayne Kennedy is truly the oracle of Chicago stand-up and his incisive commentary throughout the film would be reason enough to watch. So would Anthony Griffith’s memories of working with Bernie Mac. Or Jimmy Pardo’s explosive storytelling. And just wait until you hear Shay Shay’s recollection of the night he was propositioned after his set by – heaven help us – Jeffrey Dahmer.

Out of the Loop is a multi-layered saga that needs to be told and heard. The film had a very limited release in 2018 under the name Laugh Till You’re Winded. Michael made the difficult decision to almost immediately remove the film from circulation and re-work it.  Michael himself has had a storied career. In addition to many years as a stand-up, he wrote for George Lopez and Arsenio Hall. He kindly took time out of a busy schedule to speak with me by phone and to go behind the scenes of this much anticipated gem.


Teme: What was your inspiration for Out of the Loop?

Michael: I had a writing partner briefly. Her name was Caryn Ruby. We wrote a bunch of sketches together. One sketch we wrote is called Globolex. It was a great sketch and the best thing that we wrote.  We talked about producing it, but then our partnership broke off. In the past, a couple of times, I’ve told myself that I was going to do something and I didn’t do it. I told myself that this time, you’re going to do it. I started Laugh Till You’re Winded around seven years ago.

There was a documentary called Phunny Business about Raymond Lambert and the legendary All Jokes Aside on the South Side.  It was amazing. It was one of only two films about the scene. There’s also A Week to Kill about Hannibal Buress. It’s great too, but it’s only about Hannibal. There was a book by Bill Brady and Vince Vieceli called Stand-Up Comedy in Chicago. I came up in stand-up in Chicago and I know how good the talent pool was then and I know how good it is now. A lot of writers and producers have also come out of Chicago. Because they’re behind the scenes, no one knows about that. So I decided there should be a documentary about Chicago stand-up.

I didn’t go to film school. I didn’t have any experience doing anything like this before. It was daunting. I also made the decision that if Bert Haas, former general manager of Zanies Comedy Club, wasn’t on board, I’m not making the film. I needed his cooperation. Zanies was my home club. I worked it a ton back in the day and I respect Bert.

Bert signed on and allowed me to do interviews at Zanies. I went into pre-production and I made an announcement on Facebook, “Would anybody be interested in participating?” At first, I didn’t get much response. Then I started messaging people. At one point, Facebook thought it was spam and put restrictions on me, but that’s how it came about.


Teme: What were your guiding principles as a filmmaker?

Michael: I wanted the film to be as honest as possible. When I first conceived the film, I wanted to showcase the Chicago talent that people don’t know about. But as I started to talk to Black comics and female comics, I realized that it needs to be deeper than that. I worried at times how my peers would feel about dealing with serious issues. I got unfriended a couple of times. One very prominent director and producer unfriended me when we put the trailer out. It was a great trailer, but there were negative things in it.

I thought that maybe all people wanted was a celebration of Chicago stand-up, but that would be completely disingenuous. As a Black comic way back in the day, I had no trouble getting work. I worked the Funny Firm and Zanies and every “A” club. At the Funny Firm, they had a Monday night showcase. Len Austrevich, who ran it, would have comics in the Green Room in the basement. We would stand there like a cattle call waiting for him to choose who could go up and who couldn’t. Bernie Mac was there several times and I remember that he only got picked one time.

When I started making this film, I felt incredibly guilty about how apathetic I had been towards Black comics because I was getting mine. At the time, it hadn’t been a conscious thought. I realized later that it’s absolutely the definition of apathy. I felt like I need to make sure that – in addition to gender, and we don’t deal with gender enough in the film – that I needed to allow Black comics in particular to express themselves and include their experiences about race and not being able to get into white comedy clubs in Chicago.

When I interviewed Lil Rel at The Laugh Factory in Hollywood, he started talking about Zanies. Keep in mind, I had a long relationship with Zanies and at the time, I was working very closely with Bert to produce Zanies’ 40th anniversary film.

Lil Rel mentioned that he felt that Black comics were treated differently at Zanies. I told him, “I am going to use that.”  I’m not going to keep people’s experiences out, even if it’s detrimental to me. I had been working with Bert at my home in Highland Park when the Laugh Till You’re Winded trailer came out. I was nervous for him to see it because it included some of those negative things, but I showed it to him. He said that comics who complained about him had a choice to work for him or not. You can’t argue with that.

Teme: The film includes a lot of discussion about that persistent lack of diversity in several Chicago comedy clubs. Many of the club owners interviewed said it’s simply a business and demographics decision. But comedians see it differently. To just say it’s business and playing to demographics seemed cold to me. Where did you come out about where the truth really is?

Michael: It is very cold. I would be what I consider a safe Black act. My material was clean and it wasn’t street whatsoever. I think that the white clubs had a problem with Black acts who were more street and gritty and maybe used more profane language. They would determine who’s funny and who would work for their club. When it came to African American acts, they definitely would judge you based on the experiences within your material. There’s a lot of truth and a lot of pain in things that African American acts talk about. Black comedians offer a different perspective of America. If you were what white clubs considered too Black, you didn’t have a place there. So people like Bernie Mac had a really hard time getting into the white clubs.

Teme: One of many great things about the film is that everyone is so candid. Lil Rel Howery and other Black comedians talk about not being able to speak freely in clubs like white comedians can. Erica Nicole Clark talks about gender and has an unexpected view about Louis C.K. Chuck Sklar talks about being called a “rat-faced Jew.” As you were making the film, were you concerned about a potential backlash to all the honesty?

Michael: I started the film as a celebration of Chicago stand-up. Then you get into the interviews and people say certain things you may not have expected. You have to respect what they say. The most honest I ever am is in my creative work. When comedians start talking about hardship, especially when it came to race or gender, I knew I had to include it. I just wanted to make the most honest film that I could possibly make.

Teme: What is the state of Chicago stand-up now? Is it improving when it comes to racism and sexism?

Michael: It’s hard to gauge because everything is so PC right now. You shouldn’t say this, you shouldn’t say that. Chicago is just as polarized as it ever was. I wish I could say that it has changed. In stand-up, maybe it’s changed some. Stand-up is a reflection of society. Society is still bigoted and sexist, unfortunately. Stand-up reflects that as well.

Teme: Does Chicago reflect global issues in American comedy or is it Chicago that’s slow to improve?

Michael: Stand-up is a white man’s world. It always has been. It probably always will be. More minorities now, more women now, but still overwhelmingly white males. So I think it reflects stand-up, at least in this country, pretty accurately. But more so, when it comes to discrimination, when it comes to bigotry, Chicago is like Boston, a city where unfortunately, diversity isn’t what it should be.

Teme: When you changed the name to Out of the Loop, is that part of what you were referring to?

Michael: No, I hate that name. To be candid, I’ve had such a trying year. I’m also making a film out of what’s happened to me this year, so I haven’t been as hands on as I should have been. My producer Scott Perlman was dealing with the distributor. When we discussed the title, I told him I hate it. It sounds corny and cliche-ish.  One of the reasons I don’t like “Out of the Loop” is that there’s another documentary and a podcast named Out of the Loop. I think a name should be as original as possible. But the distributor named the film.


Teme: You initially released the film in 2018 as Laugh Till You’re Winded. Why did you decide to pull it back and re-release it as Out of the Loop?

Michael: I hated the original edit. I made a mistake. I placed it with a couple of editors early on and they disappointed me. I had trouble finding anyone that was competent. Since that was my first film experience, I didn’t have a network of producers and editors. I tried out two or three people and their attempts were really bad. Then I went back to my original editors. We were on the same page for a while, but then we started getting near the end of the edit. I’ve heard this happens a lot, but editors decide to make their film as opposed to your film. They ignored a lot of important things.

One of the biggest things that I hated about Laugh Till You’re Winded is they used a technique called jump cuts where they spliced the interviews. You could tell that it was spliced. That and some other things in the film made me think that it just wasn’t sellable. Just as important, my name is on it and I would rather it be the best it could be.

I never worked on something so hard in my entire life. So many sleepless nights. I spent a ton of my own money. I made four trips to L.A. for interviews, two trips to New York, and one trip to Vegas for Marsha Warfield. And all over the city and the suburbs. So I knew there was a better film in that footage.


Teme: What were your favorite parts of making the movie?

Michael: Being able to re-connect with comedians that I started with in the mid ‘80s. A lot of these comedians moved to Los Angeles. I’ve lived there twice, but not extensively like a lot of my friends, like Anthony Griffith who is in the film. He was the best man at my wedding. He was a powerhouse act in Chicago and everywhere else. And Paul Gilmartin who was one of the funniest comedians ever. There were days when we did ten to twelve interviews. It was a reunion.

It was also a highlight meeting comedians like Deon Cole, Lil Rel and Marsha Warfield, who is a legend. I would’ve never met some of these people unless I was making this film. There were also some stories that were told off camera like I opened for [the band] Chicago at Poplar Creek. It was many years ago and I just ate it. It was a terrible show. Jimmy Pardo is a huge fan of Chicago and he happened to be in the crowd. It’s not in the film, it’s an outtake, but we talk about how bad I did, but also that someone heckled me and that I handled the heckler really well.

One of the most touching moments was when Anthony talks about Bernie Mac. He got emotional and started crying. Everyone was crying in the room. I was concerned about using it. So I asked Anthony about that, and he said, “No, use it.” Without his permission, I would have never used that clip, but it’s the most poignant emotional interview.

Teme: Were there any surprises?

Michael: I was a bit surprised at how some women were treated in stand-up and about [how severe] the racism was as well. I just didn’t know how uneven the playing field was.

Teme: What do you hope audiences will take away from the film?

Michael: I hope the takeaway is, look at this talent! Chicago is rich in stand-up talent and it’s not just about Second City. We have a lot of rich talent that no one knew about. Also, stand-up is a reflection of life. Just because there are jokes and it’s humor and entertainment doesn’t mean you can escape realism.

Teme: How can fans best support the film?

Michael: When I or any of the producers or subjects post about the film, please share the post. Just talk about the film. Talk about what you liked. Talk about what you didn’t like. Just talk about it.

Teme: Will there be a second film?

Michael:  I have OCD, so I always have to have a high number of everything…

Teme: I totally get that!

Michael: I got a tattoo and now I have eight or ten. I have a movie collection, and it started off as… well, now I have 1,500 … 2,000 movies. I interviewed so many participants, club owners, and people from the Chicago open mic scene, that this film could be one part of a five-part series. I was going to put it to bed. I’m working on two other projects. I do literally everything. I produce, I direct. I do the audio. I’m shooting it. I’m really busy, but I’ll tell you, I’m definitely thinking about a follow-up.

For example, we only have a little bit of John Riggi in the film, but John directed and was a producer on 30 Rock, The Larry Sanders Show and The Bernie Mac Show. He came to The Bernie Mac Show right after Larry Wilmore. Then John and other producers came in and Bernie wasn’t happy with them at all. So he talked about that. He talked about getting the job on The Larry Sanders Show and in detail of where he met Garry Shandling and what they discussed. Deon Cole talked about being the only Black writer on Conan, and all these other things.  So I want to do one episode about the writers.

Teme: I would love to hear all of that.

Michael: Yes, there’s a wealth of other material that I’ve captured, so I’m now considering it.


Teme: What question would you like someone to ask you and how would you answer it?

Michael: Probably, why did I decide to make this film and why did I stick with it for so long instead of shelving it and moving on to something else? Because this is a long journey. Seven years.

Teme: How did you keep going? What was your mindset?

Michael: It was tough. I’m a high blood pressure Black man. Sixty-one years-old now. I worked so hard on that film. I wanted people to be able to see the comedians and club owners and bookers. I’m like, it’s got to be finished. I made my ex-wife promise to finish it for me and make sure it got finished if something happened to me. Once you go, you can’t be guaranteed any of that. But I thought it was a shame if it just sat on my computer.

The worst thing is – and this is what I thought when I was making Laugh Till You’re Winded – what if this is just a video file and no one ever sees it? That was definitely a fear the entire time I was making it. And in the end, since I didn’t like that edit, my fear was that that’s all it was going to be. Just a redundant hard drives full of interviews.

Teme: Everyone should support this film. Comedy in this city is a life force and people work hard to make that possible.

Michael: Absolutely. I performed stand-up for fifteen years before I left to write. Then I stopped performing for nine or ten years. Then I came back. I realized pretty quickly it’s not like riding a bicycle again. Not even close, that much time off, but it is so in my blood because I still think funny. Once you’re not performing anymore, you don’t change the way you think. Comedians see things differently. People don’t understand how special stand-up comedians are. The worst stand-up comedian is smarter than the average person.

Teme: That’s so true. You have to be able to see things that aren’t visible to the average person, communicate it to a room full of strangers and make them laugh. I don’t know what could be more difficult, but also more spiritually positive than that.

Michael: Yes, without a doubt. People are coming together for a positive experience. It’s like the audience becomes one. That’s how it is with audiences in stand-up clubs, especially when it’s really hot.

If enough people see the film, hopefully, it starts a dialogue about Chicago stand-up. Why didn’t we have this film until now to let us know exactly how great the talent pool is in Chicago and how real their experiences are?


Teme: Anything else that you would like to add?

Michael: I would like to mention that my ex-girlfriend has been behind me forever, even helped me finance the film. Her name is Jamie Nierenberg. She is a producer. As well as Mary Cunningham, who is my ex-wife, who has always believed in me.  She believed in me at times when I didn’t believe in myself. My daughter, Sydney is an actor on a TV show called Severance. She is also starring in a movie right now on Tubi. But I’m just trying to say – and I haven’t always hit this bar at all – but she’s who I want to be better for and she is my inspiration and my heart. I thank all the people who participated in Laugh Till You’re Winded. I never dreamed that I could get that many comedians’ cooperation. I really do appreciate the stand-up community coming together to help me make this film.


Out of the Loop is available on Apple TV, Amazon Prime and VOD.

Michael Alexander was kind enough to speak with me in 2018. For more about Michael’s comedy career and Laugh Till You’re Winded, please click here.

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