Ryan Dempster is a 16-year MLB pitcher, World Series champion, two-time All-Star, an analyst for MLB Network and Marquee Sports Network, and a special advisor with the Chicago Cubs.

A natural entertainer, Ryan earned a reputation during his playing days for bringing the clubhouse together with his spot-on impressions and stand-up routines. After his playing days came to an end, Ryan wanted to try to follow in the footsteps of his late-night idol, Johnny Carson. He began to explore a possible second career in comedy, taking classes at Improv Olympic in Chicago, hosting shows at the annual Cubs Convention, writing sketches for appearances on MLB Network, and coming up with the concept for “Off The Mound.”

Debuted in August 2018, “Off The Mound with Ryan Dempster” is a live, late night-style talk show featuring stories, laughs and the occasional singalong or batting practice with MLB stars past and present, actors, musicians and comedians. Complete with a live on-stage band, The Hemispheres, each set showcases guests’ personalities and who they are away from the spotlight. Since then, “Off The Mound” shows have included the two-day Innings Festival in Tempe, Arizona, Cubs Convention, and a special benefit show for the Special Olympics, with guests including Eddie Vedder, Jeff Garlin, Anthony Rizzo, Kerry Wood, Ozzie Guillen, Hall of Famer Jim Thome, Kevin Millar and Sean Casey, among many others.

In April 2020, “Off The Mound with Ryan Dempster” presented by Sloan premiered on Marquee Sports Network in Chicago. Though produced remotely, Ryan has hosted interviews with three-time AL MVP Mike Trout, former NL Rookie of the Year and MVP Kris Bryant, three-time All-Star Anthony Rizzo, three-time World Series champion Jon Lester, Hall of Famers Ken Griffey Jr., Greg Maddux and Alan Trammell, and many more.

Ryan began his MLB career with the Florida Marlins (1998-2002) and Cincinnati Reds (2002-2003) before spending nine seasons with the Chicago Cubs (2004-2012). After spending one season with the Texas Rangers (2012), he joined the Boston Red Sox, where he started 29 games and ultimately closed out Game 1 of the 2013 World Series against the St. Louis Cardinals, on the way to the Red Sox's third championship in 10 years.

In 2000, Ryan received the James "Tip" O'Neill Award from the Canadian Baseball Hall of Fame, and he was the Chicago Cubs' nominee for the Roberto Clemente Award for community service in 2006 and 2008. A native of Gibsons, British Columbia, Ryan was inducted into the Canadian Baseball Hall of Fame in 2019.