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Watch Ryan Dempster try his hand as a late night talk show host at the Cubs Convention

Dempster hosts comedic talk show at Cubs Convention

By Dakota Gardner

Former MLB pitcher Ryan Dempster has done a lot of things in his career -- he's won a World Series, he's been a two-time All-Star and he's played for five different MLB franchises, including a nine-year stint with the Cubs.

But now, he's got a new gig, and no, we aren't talking about his role as special assistant to the general manager for the North Side club. We're talking about his job hosting the new late night comedy show -- "Friday Night with Ryan Dempster."

During Friday night's festivities at this year's Cubs Convention, Dempster filled the role of a late night talk show host, performing a monologue, airing sketches and interviewing some celebrity guests.

Celebrity guests such as president of baseball operations Theo Epstein and general manager Jed Hoyer, former Cubs Mark DeRosa and Rick Sutcliffe and pitchers Jon Lester and Jake Arrieta -- to whom he was kind enough to give some excellent life advice ... while doing a pitch perfect Chris Farley impression:

Meanwhile, Arrieta was kind enough to bring a pizza along with him:

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Just like any other late night talk show host, Dempster got up to some shenanigans. When Cubs slugger Anthony Rizzo joined him on stage, he decided to toss some wiffle ball batting practice:

Which Rizzo naturally excelled at:

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Some of the other highlights included a David Letterman-style Top 10 List about reasons the Cubs hired Joe Maddon:

"We needed someone who would take the leftover Harry Caray glasses."

And some of Rizzo's opinions on his teammates:

Dempster asked Rizzo to name the best/worst of his teammates. Best dressed: Jason Hammel; Worst dressed: Travis Wood. Best singer: former Cub John Baker; Worst singer: Starlin Castro. Best tipper: Edwin Jackson; Worst tipper: former Cub Carlos Villanueva. Best-smelling teammate: Pedro Strop; Worst-smelling teammate: former Cub Emilio Bonifacio.

Dempster's long had one foot in comedy, even moonlighting as a stand-up comic a few times over the years:

I did it in Boston in 2001 for my dad because we go to comedy clubs together and he was there for Father's Day. I asked the club owner, and it so happened I was on his fantasy team, so he said no problem. I did eight minutes. I was with Florida then, and the guy on stage before me said to make a local reference to win them over. They were doing the Big Dig [a massive highway construction project] then, and I was like, 'It's good to be in Boston. I've noticed the Big Dig'--everybody cheers--'and I've seen the official state tree of Massachusetts, the three-foot orange cone.'

Back in 2004, he told the Chicago Tribune that he had two goals in his MLB career: one was to win a World Series, and the other was to host Saturday Night Live. He pulled off the first one in 2013 with the Red Sox, so he's halfway there. And, judging by his performance on Friday at the Cubs Convention, he's well on his way to the second.

Now that he's returned to the home of The Second City, there'll be plenty of opportunities for him to work on his craft. Thankfully, the early reviews were quite positive:

Check out the full highlights from Dempster's talk show in the video up top. 

Read More: Chicago CubsJake ArrietaAnthony Rizzo