It’s not unheard of for former MLB players to wind up working in TV after their baseball careers are over. Just about every network employs a handful of former pros to provide color commentary and expert analysis as a part of their coverage of the sport. But to move from the big leagues to performing stand-up comedy and hosting a late-night talk show, as former World Series champ Ryan Dempster — who spent 16 years pitching in the majors — has, is a much rarer move.
Since 2018, Dempster has hosted Off the Mound With Ryan Dempster, a baseball-themed late-night show currently airing on Chicago’s Marquee Sports Network featuring interviews with current and former MLB stars, as well as the occasional actors, musicians and comedians. And every year, he’s brought the show to the Innings Festival in Tempe, Arizona, during spring training, hosting live tapings of the show on both days of the festival.
“Sometimes I walk around here and I feel like I’m at Disneyland, just all the staff, everybody, all the people there, just smiling and having a great time,” he tells InsideHook. “And that’s what music does, what baseball does. And to see those two worlds collide is just really cool to be a part of.”
We caught up with the former Cub at Innings Festival to get his take on his former team’s big rebuild, the current MLB lockout, this year’s Hall of Fame class and more. Check out our conversation below.
The following has been edited and condensed for clarity.
InsideHook: You’ve been at every Innings Festival since it started. How did you first get involved with it, and what drew you to it initially?
Ryan Dempster: The first year, I came with MLB Network and did some stuff, actually with [Chris] Stapleton. And then I have done Off the Mound the last three years. So this year, and then 2020 and 2019 and 2018. First I got involved through Mary Beck, who was working at MLB Network. MLB Network did some work with Tim Sweetwood, who puts the festival on. And it was a no-brainer to me. There’s such this cohesive thing between baseball and music. And I love music and I love baseball. And so just being a part of it all, and having a chance for us to come out during spring training and watch these amazing bands do what they do. It was just an easy fit.
Obviously this year is a little different because we don’t have baseball yet. What’s your take on the whole lockout situation? What’s it going to take for both sides to reach an agreement?
Compromise, right? I think that’s any good relationship; compromise is a good thing. But they have to get through that together. And there’s the player in me that’s always going to side with the players, and that’s just how it is. But hopefully they’ll get through all this, and then we’ll get some spring training games going in no time, and we’ll be back playing baseball when we should be. [Ed. note: on Tuesday, after the two sides failed to strike a deal, commissioner Rob Manfred announced Opening Day would be canceled.]
A lot of guys transition to broadcasting after their playing careers are over, but transitioning to hosting a late-night talk show is pretty unique. I think you’re the only one who has done that. Was Off the Mound something you always knew you wanted to do?
No, I always knew I wanted to get into broadcasting, and I wanted to get into a different world than just talking about sports in the conventional sense. And I always felt like with players, there was so much more about them. Playing with guys, you see some of the things they go through and different hidden talents they’ve got. Guys can sing, play instruments, they’re funny, they do these different things that don’t necessarily come out on the baseball field. And so I just wanted to really be able to highlight that. And then we had the idea, and we launched during the Cubs Convention. And that was back in 2015. And then it just continued to take off, and I just realized how much I love building a show and putting a show together and bringing in these guests and being able to talk a little bit about who they are, what they do, moments in their career, how they thought about the game and the things they’re doing away from the field and off the field. It’s just been a ton of fun.
You obviously spent a ton of time being interviewed and talking to the media as a player. Do you think that prepared you at all for being on the other side of it and interviewing your guests?
Yeah, I think a hundred percent. Just understanding when you can and can’t pressure somebody for something they maybe don’t want to talk about, or maybe they do and they just need a little bit of guidance getting there, and bringing out some great stories and things like that. And listening, right? It’s about listening to the guests — what are they talking about? I’m just facilitating questions. People aren’t there to watch me at the show; they’re there to watch those guests. And that’s who I’m there to have. And that’s why I have them on, because I’m interested in what they have to say. So it really is a lot of fun for me. And I love laughing. Like when you have a guest like Sean Casey, and the entire time my smile never leaves my face and I’m out-loud laughing — what’s better than that? And just to be able to see the personality of players, just as much as who they are as athletes.
Well, and speaking of the comedy side of it, you’re not just interviewing guests, you’re doing a monologue and that kind of thing. I know you took some improv classes at iO Chicago after your playing career. What was that like, walking in there? Were people shocked to see you there when you first started?
Yeah. Well, at first, honestly a lot of people who are there aren’t baseball fans. So it’s kind of easy just to flow under the radar. And it feels like you’re starting fresh and new, like going from being at the top of my class, you’re one of 750 people in the world that’s playing baseball, to an improv class level one where you’re just the same as everybody else walking in there. And that’s the challenge. And that’s what was fun for me, is doing those challenges and doing standup raw, where you’re just green and have never been up there before. And then building routines and jokes and finding out what works and doesn’t work and not being afraid to test the waters a little bit, just push some envelopes. Like last night when I did my monologue and I was just mentioning the fact that anybody going to the Foo Fighters who watches Taylor Hawkins pound away on the drums, part of them is just going to think for a second that maybe he could have played for the Astros. You know? So stuff like that, where you’re intermixing baseball and music and just having a little bit of fun with different things. And there’s so much of that.
As a Cubs fan, I have to ask you what your take on this year’s rebuild is. How long do you think it’ll be until the Cubs have a real shot at the playoffs again?
This year. I think that with the players that they have, signing guys like Marcus Stroman, Yan Gomes, you added some guys again. I think there’s money to be spent once this lockout ends. And I think that they’re going to be forever competitive, in the foreseeable future anyways. I think when you’re a big-market team like that, you have the ability to do that. And then to restock, Jed [Hoyer] made some bold moves. And it wasn’t easy to do, I’m sure, but rather than going halfway in, he went all in and said, “If we can’t re-sign these guys, we’re going to trade them and we’re going to get prospects.” And they got a lot of really good prospects back in return, and that just adds depth. And now you have the ability, and the financial ability, to go out there and sign players. That’s ultimately what you want, and that’s a great mix to have.
Given that we’re at a music festival, I’m curious about your musical tastes. What do you generally find yourself listening to?
Yeah, honestly, I listen to everything. And I know people will say that, but I really do. I’ll get up in the morning with my kids before school and I’m playing Frank Sinatra as they have cereal and get ready for school. And then later in the afternoon, there’s some Eric Church belting out in the house. And then I might be jamming some Disney songs. If you don’t talk about Bruno right now, then you’re not with it. That’s what’s going on. And then I love rock and roll. Like I loved, loved, loved the Foo Fighters last night. They just kicked ass. Dave was so great. The whole band was great. The energy they brought was just what everybody was looking for. St. Vincent was amazing. So good. And I got to see a little bit of Dashboard Confessional. I got to see a little bit of Black Pistol Fire, and I thought they were awesome. So there was just a lot. I just appreciate music so much, the ability to grab an instrument, make that kind of noise. And then to command a stage in front of a bunch of people is just something I admire so much. So, yeah, I think at the core of me, if I had to listen to something, it would probably be country, just because I grew up with uncles that all played country music, but I just love everything. Sleep on me throwing out some Dr. Dre, or some Snoop Dogg every once in a while. I was a Super Bowl halftime fan. That was good.
You’ve obviously had plenty of highlights during your playing career, but what would you consider so far to be a highlight of your broadcasting career, whether it’s in the booth or doing Off the Mound?
I really love doing Off the Mound. That 2017 Cubs Convention after winning the World Series was my favorite show I think we’ve ever done. We just had so many great skits and guys singing with me and all that kind of stuff. We had a blast. Doing a standup set and coming off stage at Gotham Theater in New York and handing the mic over to Jim Gaffigan was pretty cool. I know I wasn’t on the Playbill of “Jim Gaffigan with Ryan Dempster opening,” but in my mind it felt that way.
What’s your take on this year’s Hall of Fame class? Obviously, there was a lot of talk about it being a referendum on a lot of these players who were accused of taking steroids. Do you think that players like Barry Bonds, Roger Clemens, Sammy Sosa, do they deserve to be in the Hall of Fame?
The first two that you said for sure. I think both those guys were the best player and best pitcher I ever saw. Unfortunately, there’s always going to be these asterisks, and the people who vote get the decision, right? I’m just a player who played the game. And I always say I was very, very lucky to come through that era as a prospect and not a suspect, and have to make those choices. But to each their own. And it was a different world back then, and things were going on in the game. And I’m just not a very judgmental person. I feel like if I were going to really do that deep dive, I think I feel like there’s plenty of players that are already in the Hall of Fame that used performance-enhancing drugs. So where do we draw the line, right?
Assuming we do eventually get baseball this year, who do you think we’ll be seeing in the World Series this season?
Oh, I have no idea. There’s still too many good free agents out there, but yeah, I think what the Mets have done is pretty impressive, signing the players that they got. When you get a guy like Max Scherzer, that’s going to be a huge factor. The team with the best starting pitching, that’s who I’m going to go with.