Former MLB All-Star Ryan Dempster Wants To Make You Laugh

When Ryan Dempster first started taking improv comedy classes, his fellow students didn't recognize him.

"First class, no," the two-time MLB All Star and World Series champions says. "Second class, when I got into level two, they — it started to be known that I did play. And they're just like, 'Why are you here? Did you fall on financial hardship?' "

No, Ryan Dempster (who according to Baseball Reference made $89 million in his 16-year MLB career) has not fallen on financial hardship.

But for those who have really known him, this new career makes a lot of sense. Take his childhood babysitter.

"She was like, 'You know, when I found out you were a baseball player, I was like, "Oh, OK..." But then when I found out you started to do standup comedy afterwards, I was like, "Oh, I totally get it!" ' " Ryan says.

'I Just Got Hooked'

Growing up in Gibsons, British Columbia, near Vancouver, Ryan Dempster landed a pretty sweet part-time job.

"I worked at a video store when I was in high school, and one of my perks was I got to take as many movies home on a Friday and Saturday night as I wanted," he says. "And so, me and my brothers, it was always like, 'Oh, let's get this' or 'Let's get this.' And you know, 'UHF' was one that we always would take home that night and watch it.

"And then, as we got older, you started getting into Mike Myers and Jim Carrey, and we'd watch them over and over. And we barely talked like normal to each other. It was always some sort of movie line quote."

"I’d come crawl onto the couch with him, and he’d be watching Johnny Carson. And I was just like, 'Oh, this is awesome.' And then I just got hooked."

Ryan Dempster

But it was Ryan’s father who introduced him to the entertainer who would inspire Ryan’s second act.

"There would be nights where I'd be watching a hockey game or something late, and I’d come crawl onto the couch with him, and he’d be watching Johnny Carson," Ryan says. "And I was just like, 'Oh, this is awesome.' And then I just got hooked."

Comedy And Baseball

Now, it’s not like from that moment forward Ryan Dempster was set on becoming the next Johnny Carson or hosting his own late-night TV show. Not back then. Not yet.

Ryan was focused on a career in baseball. He had a strong right arm. And, in 1995, about a month after his 18th birthday, he was drafted by the Texas Rangers. By the age of 21, he was in the Big Leagues, pitching for the Florida Marlins.

But he brought his sense of humor to the job.

"I was the guy that was always trying to figure out a way to keep it light," he says. "I don't know if it was because, as a starting pitcher, I had four days off in between, so it was a lot of free time. But I always saw the value and the importance of laughing a little bit. You know, we’d land somewhere at 3 a.m., and I’m gonna grab a microphone from the bus driver and play tour guide."

(For example, Ryan says he might tell his teammates: "All right, ladies and gentlemen. Welcome to New York City. Now, we want to remind everybody, New York City is the place that never sleeps. That's right, the city that never sleeps. The Big Apple. But that doesn't mean that you shouldn't sleep, either. We are professional baseball players. You have a duty to do — that's to go out there and perform on the field.")

But during his rookie season on a struggling Marlins team, Ryan had to learn an important lesson.

"I remember we were in Houston," he says.

The Marlins were losing badly to the Astros. Ryan was on the bench with some other players, including a fellow starting pitcher.

"We're all kind of huddled around, and he told a really funny joke — probably 'cause earlier I was telling a joke and I started it — and I looked down the bench, and my eye-line is with Jim Leyland, who is our manager.

"And he's put out — we're terrible. We ended up losing 108 games that year, I think. We were 54-108 or something like that. And he always smoked cigarettes in the dugout. And he took this big drag off his cigarette, and he just chucked it on the field and he walked down the tunnel."

After the game Ryan and his teammates were in the locker room when they heard Leyland approaching.

"He wore metal spikes, which I thought was so awesome — that your manager's — he's ready to take you out of the game and put himself in if he's, like, that mad, you know?" Ryan says.

"And you just hear this like, 'Chick, chick, chick, chick. Boom' — and the doors just kick open. 'If I ever see another one of you pitchers laughing when we're getting our a---- kicked, I'll have you out of here so fast your head will spin.' And he unleashes on us, like over and over and over. And then he'd stop. He'd be like, 'Guys, guys, listen. I'll go 0-162 with you. No problem. But not like that. You're not going to laugh when we're out there getting our tails whacked around. You better learn to have respect.'

"So I'm just so embarrassed. And then he had the best line ever was — after leaving the clubhouse and coming back in five times, on the fifth time he said, 'If I come back out here and there's anybody in this locker room, then I'm going to call the cops and have you arrested for impersonating Major League Baseball players.'

"So good. Just so good. I don't even know if I showered. I was out of there so fast. I hid from him for, like, four days."

Lesson Learned

So rookie Ryan Dempster was learning when it was and wasn’t time to joke — and he also learned who to leave alone when they were having a bad game.

"And, you know, you got other guys on the team who can strike out and they come back to the bat rack, and then they sit on the bench, and then you just walk over and you're just like, 'Hey, dude. Are you sure you're a left-handed hitter?' ”

Ryan went 1-4 his rookie season. But the next year, he finished 7-8, tying him for the second most wins on the team. In his third MLB season he made the All-Star team for the first time.

And in his fourth season, on a trip to Boston to play the Red Sox, Ryan would make a very different debut.

Ryan was scheduled to start the first game of the series for the Marlins. It would be one of his first times pitching at Fenway Park.

Was he nervous?

"Um, yeah, but it's, like, nobody — like, we're with the Florida Marlins. They don't even know we have a team in Florida," he jokes. "We're, like, nobodies."

The night before he was going to start against the Red Sox at Fenway Park, Ryan Dempster, his dad, and two teammates stopped by a comedy club at Faneuil Hall.

"We kind of realized, 'Hey, man, it's open mic night. This is cool,' " Ryan recalls. "And I just said, 'I'm gonna go do this.' And I didn't tell anybody. And I just went over, talked to the manager and said, 'Hey, I'm Ryan Dempster, pitcher with the Marlins. I'm in town. I got a couple of teammates. Any chance you could let me get up there for a little bit?'

"He was like, 'Get the f--- out of here.' And I was like, 'No, I am.' And he goes 'Oh, yeah, for sure you can.' And then he introduced me as tomorrow night’s starting pitcher. I sweated like cra[zy] — I was way more nervous than the next day at Fenway Park."

Ryan went on stage. He talked about his trip to Boston.

"I was like, 'Yeah, we did this tour with me and my dad. Saw the Big Dig,' " Ryan recalls. "And everybody cheered the Big Dig like it was some sort of spectacular moment, you know? Like, the Red Sox had won the World Series was the equivalent. And then they laughed a little bit, and then nobody threw any tomatoes at me."

Ryan and the Marlins lost the next day. He can’t tell you too many details about that game. He says his memory works in unusual ways.

"I don't even know what day of the week trash day is, but if you want me to quote Austin Powers for days, it's just, like — it's nonstop."

(In case you don't believe him, listen to the audio version of this story by clicking the play button next to the headline at the top of the page.)

After that open mic night at the comedy club in Boston in 2001, Ryan Dempster didn’t get back on the stage. At least not for a while.

Next Stops

In 2004, Ryan signed with Cubs, which got him to Chicago, a city famous for its comedy scene. That, Ryan says, was just a coincidence — but he did continue telling jokes and doing impersonations for his teammates.

In 2013, he won a World Series with the Red Sox. And then, after 16 MLB seasons, he retired.

"Once I got done, I really had the vision of the late-night talk show," he says.

That’s when Ryan joined that improv class where his classmates wondered if he’d fallen on financial hardship.

He also returned to standup. At first, Ryan says he was hesitant to talk about his baseball career on stage. He even performed at open mics under an alias.

"But one of my friends — Andy Engel who runs the Gotham Comedy Club — he's like, 'Share those — like, you have experiences that those other comedians don't.' "

So Ryan started joking about baseball. And, meanwhile, he built up his experience on TV by working as an analyst for MLB Network.

And then, in August 2018, Ryan debuted "Off The Mound with Ryan Dempster," his own late-night style show.

It features a live band, interviews with baseball players and other celebrities and, of course, Ryan telling jokes.

Ryan calls the show his own “fun little take” on Johnny Carson.

At first "Off The Mound" was only a live event. Then it was also streamed on the internet. But this year it moved onto the regional Marquee Sports Network, which broadcasts Cubs games.

Because of the pandemic, Ryan hasn’t been able to film in front of an audience. But he’s still putting out episodes from home.

On the TV premier this past April, Ryan used a doll to teach three-time AL MVP (and father-to-be) Mike Trout how to change a diaper.

"There is a comedian, who said, 'Laughter,' — I think it might've been Jim Gaffigan — he said, 'I believe that laughter is the best medicine, after you get real medicine.' And it's true," Ryan says. "If we can give a little bit of laughter and a little bit of levity, then I think that’s really important."

More than three decades since he started watching Johnny Carson on the couch with his dad, Ryan Dempster is now in the host seat himself. He says he knows he’s still got a lot to learn, but it seems like he’s right where he’s supposed to be.

Ryan Dempster is a special assistant to the Chicago Cubs and an analyst for MLB Network and for Marquee Sports Network, where he hosts "Off The Mound" every Friday. You can also catch the "Off The Mound" podcast here.