The first time Ryan Dempster did a standup gig, it was at Faneuil Hall in Boston, an 18th-century marketplace that has been the site for speeches from Samuel Adams to former president Barack Obama.

The next night, Dempster was the starting pitcher against the Red Sox at Fenway Park, the oldest major league ballpark still in use and the place where Babe Ruth started his career and where Carlton Fisk hit his famed 1975 World Series home run.

Two historic locations that test the nerves of any performer, and Dempster did them in back-to-back nights.

“I was way, way more nervous during that standup than I was for that start,” Dempster recalled. “I remember being so nervous for that standup. I couldn’t believe I was doing that, versus pitching at Fenway Park, I was like, ‘Oh, yea, this is going to be tough, but I can do this.’”

That’s the essence of Dempster’s dual career paths; as he wrapped a 16-year tenure as a major league pitcher, Dempster was already at work on the next phase of his professional life.

“It was something I was interested in when I was playing,” Dempster said of his standup and talk show career. “I would go to live improv shows at Second City, comedy shows, or different standups, and then when I got done playing and started going down this road, I thought the best way for me to do this is to try and gain as much knowledge about it, so I signed up for a class at Improv Olympics.”

In the years since he retired from playing baseball in 2013, Dempster has transitioned from the mound to the stage, doing work on television and in standup and improv comedy. Like most baseball players, he grew up loving the sport and dedicated his life to playing it, but Dempster also grew up with a love of comedy. He jokes that his childhood babysitter was surprised to see him turn out to be a baseball player instead of a comedian.

Dempster credits his sense of humor to his family, and his love of standup and late-night show comedy comes in part from staying up as a kid to watch Johnny Carson with his Dad.

“I grew up in a family, an extended family too, that really believed in the value of laughing and humor,” Dempster said.

Between his Dad, his Mom, and his two younger brothers, dinners at home were filled with jokes and impersonations. Dempster took his sense of humor with him to the clubhouse after the Rangers drafted him out of high school in 1995 and as he went through the minors and and broke into big leagues. It wasn’t uncommon for him to grab the mic on the team bus and play faux tour guide or to crack a joke to lighten the mood when a teammate was struggling.

Once in Houston while he was pitching for the Cubs, Dempster helped then-teammate Jacque Jones out of a back-and-forth with an unruly fan. Jones was struggling at the plate at the time, and even though he was playing good defense, the fan went after Jones about a bad throw to home plate. Dempster tried unsuccessfully to intervene at first, and then eventually turned to humor.

“’Jacque, did you see your throw? It did suck,’” Dempster told his teammate. “It disarmed him with the fan, and he took it inside, and that was a moment where I could trust my teammate. I knew him well enough, and he could trust me, but I needed humor in order to diffuse a moment between a fan and a player over throwing a baseball.”

Like his baseball career, Dempster has always taken his comedy seriously. It’s more than just trying to be funny or remember moments that made him laugh when he gets on stage. Dempster started taking improv classes late in his baseball career and began pursuing standup at around the same time. He carries a notebook with him most of the time, so that when a joke comes to him or something happens that he thinks he could use on the stage, he is able to write it down. Doing that, Dempster said, is a major part of developing a successful standup routine.

“It’s a lot of work,” Dempster said. “These people that do standup comedy that finally make it big, it’s hours and hours, days and days of traveling around the country and trying out different gigs at different clubs. It’s a lot of hard work to get where they’re at.”

These days, Dempster has his own show and podcast on the Cubs’ television network, Marquee Sports, that developed from a gig he had at the Cubs fan convention held every January. Called Off the Mound, Dempster models his show after the late-night style shows he grew up watching. On any given night, his guests might range from baseball stars like Mike Trout to rock stars like Eddie Vedder.

The idea for Off the Mound came a few years ago as a way to connect fans with the players during the Cubs’ annual winter convention. Along with being an avenue for his humor and for his desire to have a late-night style show, Dempster has seen Off the Mound as an opportunity to further humanize the players and, hopefully, make fans less apt to boo them when they struggle.

“It’s the only job where it’s totally legit for people to boo us,” Dempster said. “Can you imagine if I just walked into an emergency room and someone’s doing surgery, and I’m just booing the doctor because I didn’t like his incision. I thought it should have been horizontal instead of vertical? I’m going to go into a courtroom and start booing the lawyer, they’re going to kick me out. In sports, it’s like, yep, no problem.”

Dempster hopes that by bringing players on, he can show them their sense of humor and some of the things that make them regular people. Like new father Mike Trout changing a diaper.

“You get to highlight the most important person, and that’s the guest,” Demspter said. “The great work that they do in their charities, the type of people that they are, the funny guys that are out there that people don’t even realize how funny they are.

“Sports are very results-oriented, and we get caught up in that. They’re still humans out there. They’ve got emotions and they’re giving everything they have, and they’re trying to succeed. I still understand that, and I haven’t lost sight of that, so if I can just get people to see them as the humans that they are. While we admire what they did and we look up to that, there’s still a human on the other side of that, and maybe we can be just a little bit more compassionate in times where they don’t do their job or when things aren’t going that well.”

Dempster hopes for Off the Mound to eventually have a live audience in a theater. He has been to Letterman and Colbert in person, and that’s the kind of vibe he wants for his show.

For now, those dreams are on hold because of the coronavirus, but Dempster has made the most of doing his show remotely. Since shifting to Marquee, Dempster has done seventeen episodes with an audio version of each on available in podcast format.

“I always liked the live studio audience, the genuineness of it, having people in there,” Dempster said. “To be in there, you just smile the whole time, you laugh, and you leave with a little bit of joy.”