By: Nick Macksood
This Week: So what part of Chicago did you grow up in?
Damon Williams: Right on the south side of Chicago, Sox fan. No Cubs here.
TW: Were there any comedy clubs you hung out in frequently when you were starting out in Chicago?
DW: My career began at the club All Jokes Aside, which is a historic club for urban and black comedians. Back in the day it launched the careers for a lot of people and maintained them as well. Everybody from Sinbad to Chappelle, you name it. And there’s a documentary called Phunny Business that documents that club.
TW: Being from the midwest myself, I’ve always felt that Chicago breeds a certain kind of person: tough, dedicated. Is that true of comedians, too?
DW: Yeah I mean, if you look at the spectrum of comics who were born and raised here in this area or went through the improv scene with Second City, Improv Olympics you can see a common thread. Melissa McCarthy is now the new hot talent from the Chicago area, but there’s also Deon Cole, Deray Davis–guys that I worked with growing up–and Bernie Mac, of course. All these types of comics carry a certain swagger that comes from their environment.
TW: Did you ever work with Bernie Mac at all?
DW: Yeah, I was the opening act for the original Kings of Comedy Tour so I did thirty dates with those guys. But prior to that, I was already sort of in his camp so whenever I was out in LA–where he had a weekly showcase–I would sometimes fill in a spot or do some hosting. I had a real close relationship with Bernie.
TW: That’s nice. What was Bernie like?
DW: Bernie was a genuine person. If you watch his sitcom, that’s exactly the type of person he was. His work was really an authentic portrayal of the man he was: no nonsense, a straight shooter, very funny, creative and driven.
TW: What do you learn from touring with guys like Bernie Mac or the Kings of Comedy?
DW: You always take a little something from your peers or your mentors when you go around like that. How to be a professional, how to control a really large crowd like that, you know, just how they took care of business.
TW: What made you want to get into comedy? Was it something you’d always envisioned or did you just decide to go for it one day?
DW: Well I’d been interested in it from a fan’s standpoint for a very long time. I’d followed comedy since I was kid, watching stuff like The Tonight Show in the 70s and 80s. You know, guys like Rickles, Rodney Dangerfield, Bill Cosby, Red Fox, and of course, Richard Pryor. But then Eddie Murphy in the mid 80s really sparked my interest in the way that he took it to another level.
What made me actually pursue comedy was the Def Jam circuit and all the opportunities that came with it. I was a former Subway franchiser and one day I sold my shop and just took every opportunity I had to try my hand at comedy, give it a shot.
TW: Did you ever do any open mic stuff before that point or did you just go up there cold and start telling jokes?
DW: Actually, so when I got my start at All Jokes Aside in 1992, that was only my second time ever trying to tell jokes to a large group of people. It was only the night before where I’d heard there was a spot nearby that was doing some open mic nights and I was able to get up there cold. That night was when I first tried out the routine I’d been working on that I’d eventually perform at All Jokes Aside, which was at the time the real dominant, high profile open mic session in Chicago, it was hosted by Del Gibbons. I went up and it went well, so I’ve been going up ever since.
TW: Let’s move to the Comedy Fest. The MVCF shows are really the only comedy shows on the island. This is the sixth year in a row now, correct?
DW: Yes, and I’ve been with them since the first one, seeing it blossom and grow. Last year was excellent, we had sold out, standing room only shows every night. We were turning people away, there wasn’t enough room. Moving to the Lampost made all the difference. It used to be held at an older theater, kind of off the beaten path. But once we moved into downtown Oak Bluffs, it started skyrocketing.
TW: And quite a lineup too–do you work with these guys or tour with them on a regular basis?
DW: Yeah, we’re all friends, all colleagues. Steve [Capers] and I were doing a monthly showcase in Chicago called Funny First Saturdays and we’ve constantly booked some of the same faces you’ll see here.
And that’s the great part about this show, the chemistry between us. I mean, we’ve all known each other for a long time and since we stay in the same house on the island, our personalities really blend in the time you don’t see us on stage. Some of us are married, some not. Some have families, children; there are men and women, so the dynamic is always moving. It really should be a reality show, it’s that interesting. Some of the funniest things happen off stage.
TW: I think your show is going to cross paths with the president’s vacation, isn’t it?
DW: He is. His vacation usually coincides with the Comedy Fest. In the past, we’ve gotten glimpses of the motorcade. One of my friends peeked through the bushes and got some photos of him playing golf. The irony is, my other friends Chris Spencer–who brought Ray Allen, Alonzo Mourning and a couple other guys to the show–the next day they went out to play golf with the president.
I know one of the president’s right hand guys, so annually I always extend an invitation to him to come to the show, it just hasn’t worked out yet. I hope this year, being his last presidential vacation, he’ll have some time to come out. And if he continues to vacation here as a civilian, we’d love to have him come to the show. We know he’s a comedy guy.
TW: Where can we find you? Are you touring now after the MVCF or are you working on anything?
DW: I just wrapped a film that will probably go direct to Netflix and DVD called Not Another Black Movie. We just wrapped Sunday, so it’ll probably be out Thanksgiving weekend, Black Friday. You can hear me on my morning radio show, Seriously Ignorant News, every Tuesday. Damon Williams, you can find me on social media–except for Twitter. I’m Damon William on there, somebody’s using my name so I gotta try and get my “s” back. But I’m always touring, always doing shows, and looking forward to coming back to Martha’s Vineyard.
