On Monday, April 3, Best Night Ever celebrates its third anniversary. Not every stand-up showcase reaches that milestone, but Best Night Ever is known for living up to its name. Every Monday night at Gman Tavern, producers Sam Ash McHale, Mike Cronin, Dave Losso and Mike O’Keefe put on a quality line-up of rising and established stars. Nationally known touring comedians often drop by for a guest set. And it’s completely free.
Earlier this month, Time Out Chicago called Best Night Ever one of Chicago’s best places for comedy and an evening where you’re likely “to spot the next Cameron Esposito or Kumail Nanjiani.”
How has the showcase found success so fast and consistently? Sam, who was one of the show’s creators, kindly spoke with me by phone about how she got into comedy as a non-comedian, what it takes to build a thriving showcase with an emerging national reputation, and why this Monday night will be the best of Best Night Ever.
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Teme: How did you get involved with Best Night Ever and how did the showcase begin?
Sam: I’ll start off by saying I’m not a comedian. I’m just somebody who really enjoys the scene. Five years ago, I started going to local shows and getting involved. I was working at The Metro as a promotions intern. There was a comic who is in Detroit now, Mike Stanley, and he was looking for an intern to help out with his shows, so I told him I would help out. I helped him do all the promoting and whatnot. I really liked it, so I got into booking.
At the time, a few other comedians who have since moved to New York, were trying to find a place to start a show. I said, “Why don’t we team up? I’ve got this place [Gman Tavern] that’s right next to my work.”
Teme: Congratulations on the third anniversary show! What do you have planned?
Sam: We’re really excited about it. We’ve booked our favorite comics, although we tried not to book the same people from the previous anniversaries.
We also decided to change it up a bit. Each producer chose two comedians and in between those sets, the producers will each do a set. I’m not entirely sure, but I may even do one. I’d like to at least introduce the people I picked and tell people why they’re my favorites.
We’ll have our $3 drink PBR specials like always. We’ll also have gifts and swag.
Teme: Who are the comedians who will appear?
Sam: It will be Ricky Gonzalez, Nate Burrows, Jason Melton, Allison Dunne, Danny Maupin, Cleveland Anderson, Gena Gephart and Spark Tabor.
Teme: How did you originally decide on the name Best Night Ever?
Sam: Best Night Ever was thought of by one of our former producers, Alex Stone. The original idea was to have a show and a dance party afterwards. That never really came to fruition, but the name stuck.
Teme: I’ve heard and read that Best Night Ever really is one of the best. What would you say makes it stand out?
Sam: I think it’s because we have such a great team. Our producers are also road dogs. When comedians from out of town want to come to Chicago, they already know our producers and always reach out. We’ve had people who’ve been on Comedy Central and the Tonight Show and all these other national headliners come in.
Teme: I’ve noticed many names like that on your line-up! What is your role as producer?
Sam: My main role is as head booker. If anybody wants to do the show, they’ll send their clips to me. I also try to book newer comics. I want to give them a shot, even if it’s just six minutes. Just to help them get things going and get themselves established in this city.
Teme: How would you describe each of your co-producers?
Sam: Dave Losso joined Best Night Ever in 2015 and is our second longest-term member. I like to refer to him as my “ride or die.” He keeps me grounded when I’m worried about people coming to the show or when there’s some sort of snafu that makes you want to give up on all of it. He’s always there being reassuring and he gets my head back in the game. He’s a very funny comic. One of the funniest in Chicago, I would say.
Then we have Mike Cronin, who’s also super fun. One of the best hosts you can ever see. He does a great job getting the crowd going. He’s a road dog. He’s on the road most of the time, but even when he’s out on the road, he’s promoting the show from wherever he is. He’s a very, very hard worker.
Mike O’Keefe is our newest producer. He’s been with us about a month, but we’ve known him for a while and knew that he was going to be a good fit. He’s very passionate and driven. He helps out a lot with booking suggestions, too, which is a load off my mind.
All the producers are very driven and hard working. They make the show fun regardless of what size the audience is. We could have ten people or we could have fifty, but they always get the crowd going and it’s always a fun show.
Teme: What is the secret to creating a successful showcase?
Sam: I would say hard work and determination. Since I don’t do comedy, I don’t need to focus on anything other than the audience. I just want people to see the great local talent. So it’s paying attention to the scene and who works well together; just trying to put on the most fun show possible.
Teme: I wanted to ask you about the art of the line-up. How do you put together the evening?
Sam: I usually book the headliners first. Then I book comics who I think go well with the night’s headliner. If there’s somebody coming in from out of town, usually they’ve been in touch with me ahead of time. But we also try to leave room for anybody last minute who says, “Hey, I’m coming in from out of town. Do you think I can have a spot?” I try not to put in too many people. We generally have five at the most.
Teme: What have been the biggest rewards and challenges?
Sam: One of the biggest challenges is the location in Wrigleyville. We have very strong audiences, but we’ve had to cancel a bunch of times because of games. We have to cancel the two shows after our anniversary show because of the Cubs’ season opening.
We’re going to cross our fingers and hopefully we can get people to come in regardless of whether there’s a game or not. That would definitely be our biggest challenge. The rewards are hearing people talk about the show, and making connections with comics. We recently had Kurt Metzger come in as a headliner. He’s a writer for Amy Schumer and Chappelle’s Show.
Teme: What has surprised you about producing the showcase?
Sam: This show is like my baby. It’s a lot harder and a lot easier than you would think. It’s hard because there are so many amazing showcases in Chicago and a lot of them fall on Monday. Getting people out to your show while wanting to be supportive of your friends who are running the other shows can be a difficult thing. Sometimes you just have to focus on you at that point. That would be the hardest part.
We may have a night where a lot of people come, or a night where maybe there are five people but they’re laughing the loudest of any crowd we’ve ever had. We just want to keep producing good content regardless.
Teme: What is your advice for someone who wants to create a showcase?
Sam: You have to have the drive and passion going into it.
Location is always something you have to look into. You can’t just find a place and be like, “Oh, here’s an open room.” You have to think about whether this bar is going to be packed in a good way or a bad way. Our having Cubs fans come in is not necessarily a good thing. They’re not always comedy fans and may be there just to watch the game or drink. That’s definitely a difficult thing for us.
You also have to think about the people you want to work with and who will make the show a priority and put in the time and effort to really make it great.
It can be difficult with so many comics in the city because you want to book them all. Everybody wants to do the show, but sometimes you just have to make executive decisions. Sometimes you have to be a hard-ass.
Teme: What inspired your own love of comedy?
Sam: I’ve loved comedy most of my life, but who doesn’t? When I was younger, I would watch Saturday Night Live. As I got older, I had access to iTunes and I listened to more comedy albums. I’d also hop onto Pandora radio stations and learn about new comics that way. When I turned 21, I was able to check out all the comedy clubs and shows that our city has to offer.
My first comedy show was Chicago Underground Comedy at Beat Kitchen at one of Cameron Esposito’s last shows there.
I started talking to comics and checking out other shows. I fell in love with comedy. There was a time when I was at a show almost every night, or multiple shows a night. At the time it wasn’t really tiring, but it does take a toll on you. There’s just so much to see and do here. But I still love it just as much as I did five years ago when I started going to shows.
Teme: I’ve had people say to me, “I can’t see comedy that often because I’m on a budget.” More people need to know there are great shows that are free or very inexpensive. Budget doesn’t have to be a barrier.
Sam: My first year going to comedy shows I maybe spent $30 the entire year. You don’t need to go to a big comedy club. Not to say a Comedy Bar or Laugh Factory isn’t worthwhile, but there are options.
We have people like Hannibal Buress and TJ Miller coming in and performing multiple times a year. You just have to keep your ear to the ground.
You don’t have to go to the big clubs to see great comedy. Sometimes all you need is a back room and a bar with cheap beer and some good friends.
Teme: What else would you like everyone to know?
Sam: I hope people will give us a chance and give all of Chicago comedy a chance because we have such great comedians here, people who go on to do really amazing things.
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Best Night Ever 3-Year Anniversary Show is Monday, April 3 at 8:30 p.m. at Gman Tavern, 3740 N. Clark St., Chicago.
Best Night Ever’s free weekly stand-up showcase is every Monday night (with a few exceptions during Cubs season). Follow Best Night Ever on Facebook and Twitter for all details.