Feature: Ryan Dempster and Off The Mound (Innings Festival)

Wow . . . where do I even begin on this one. If you follow our site, then you know if there is one thing I love more than festivals it is baseball. Innings Festival, which takes place in Tempe Beach Park in Arizona, combines music and baseball into one epic festival weekend. There is fantastic music on the lineup (and you will be able to read more about that in our post-festival recap), but this very early morning post is about one of the aspects of Innings that makes it so unique – Ryan Dempster and his “Off The Mound” talk show that takes place two times a day on the “Left Field” stage.

If you read our recap from last year, you know that “Off The Mound” provided some of my personal favorite moments of the weekend and probably of festival season as a whole. Also a whole lot (really an excess amount) of baseball fangirling. One of the best things about “Off The Mound” is that all of Ryan Dempster’s guests are super excited to be out there. Last year Jim Thome provided a hilarious moment when he continually peeked around the corner and waved to the crowd while Dempster was trying to introduce him and then finished off his time on the stage absolutely launching signed balls off a tee on the stage into the crowd with a real bat. (Photo credit to Dempster’s team).

Jim Thome_Ryan Dempster_Innings Fest 2019

So, when Living The Fest Life got the opportunity to chat with Ryan Dempster we jumped at the chance. I also may or may not have screamed like a kid in my office.

For those of you who aren’t familiar with Ryan Dempster – first of all what kind of baseball fan are you?? Dempster retired from MLB at the end of the 2013 season after pitching for 15+ seasons. He is a two time All – Star and a big part of the 2013 Cubs team that brought the World Series title back to Chicago. Fans and players alike know Dempster for his fun off field personality as well. What you may not know about Dempster is that he has been working on the comedy side of things for quite some time.

We chatted with Ryan about baseball, “Off the Mound” and his post-baseball comedy career yesterday. Here are some highlights:

Let’s start with “Off The Mound” – I got to experience the show at last year’s Innings Festival, but can you tell us a little about the concept for those who aren’t familiar? 

Ryan explains that “Off the Mound” is “kind of our idea of a late night talk show format with the band, music, guests – coming out for a few minutes talking and sharing stories about who they are as people not just as baseball players” sharing their “hidden talents” and connecting with the crowd.

And “Off The Mound” was something that existed before Innings Festival right? How did that start and how did you become involved with Innings Festival? 

Off The Mound’s connection to Innings started a few years ago when Dempster came to the festival as part of a crew meeting with sweepstakes winners. He got to see Innings unique baseball/music concept and approached festival management. He explains that he was like “hey I have this show I do and I approached the festival with that” and with the idea of “break[ing] up the day with a couple of shows.” It worked out well with the festival setting up a “stage for us out there in left field with all the baseball stuff.” Dempster goes on to describe how last year was really a “ton of fun . . . capping it all off with Eddie Vedder.”

Author Note: During the same “Off The Mound” show that saw Thome hitting balls to the crowd, there were some other huge guests. Thome was followed by Cole Hamels, Sean Casey (who was hilarious) and a surprise appearance by . . . Eddie Vedder. He and Sean Casey are apparently buddies, and he came out carrying a Sean Casey cut out – backstory on that here. 

Sean Casey_Eddie Vedder_Ryan Dempster_Innings Fest 2019

That was really fantastic and such a fun time for the crowd. Speaking of Eddie Vedder Last year, you had a ton of amazing guests on “Off The Mound” at Innings – do you expect a similar lineup this year and more generally do you have like a bucket list guest you would love to have on the show at some point? 

Ryan explained that he expects to have similar guests this year, that the “Off The Mound” lineup is “loaded with stud baseball players, hall of famers, All Stars, Gold Glovers, and that we may have a surprise guest or two . . not really sure” but that it will be similar but more of a baseball heavy guest list this year.

As for the bucket list question – he chuckles a little before saying that he definitely has a bucket list. And starts by naming Rickey Henderson as someone he would “love to have on the show.” Going on to say that “as far as a non baseball bucket list, I would love to branch out . . . on the entertainment side someone like Kevin Costner who has made a ton of baseball movies” and has had a baseball “impact on the entertainment side of things.” Dempster also mentions how cool it would be to have Robert Redford (from baseball classic “The Natural”) as a guest and then also mentions Garth Brooks.

There were some great moments last year – I think Jim Thome absolutely launching balls into the crowd was one of my favorites. 

Author Note: In my memory he had a wiffleball bat – but Ryan explains a really cool bit of the whole backstory on how this fun moment happened, quickly reminding me that it was a real bat. Ryan explained that he had brought up the idea to Thome before the show and asked him if he would be open to it. With Thome agreeing to do it with a real bat (rather than metal) which he thought showed why the guy is a true champ – up there willing to just go yard off a tee without the benefit of a metal bat. Given how far he hit the balls with a traditional bat, over our crowd and into the unsuspecting people listening to music on the other side of the fest – I can’t imagine what he would have done with a metal bat.

So, if I understand correctly, you have had some connections to comedy for quite some time – can you tell us a little about your first post-baseball moves and also how you came to comedy? Was it something you were always interested in? 

Ryan explains that he has always loved comedy and has been going to comedy clubs since he was 18. He describes being a big fan of Johnny Carson and then reminisces about when he was in seventh grade and his dad let him watch Eddie Murphy’s “Delirious” stand up show late on the night of his birthday after his mom had gone to bed. He talks about how he has always loved stand up comics and that he has goofed around and tried his hand at it for years.

Here we started talking about the time he tried his hand at an open mic night in Boston in 2001.

They introduced you as the starting pitcher for the opposing team for the next day didn’t they? 

Yeah. They did. It was a tough crowd already.” He claims that he “bombed that night and bombed the next day” at the game (which I am not sure I believe). But laughs saying that his “comedy performance was a lot better than his performance on the field the next day.”

Beyond that can you talk to us a little more about the work you have put in on the comedy side of things? 

I started taking improv classes at iO (an improv theater in Chicago) and working with Second City and then there was all the Harry Caray stuff.

For those who are not familiar, Dempster does a fantastic and very funny impression of Harry Caray (here’s a video from the time he did it in the booth in full costume). As a baseball fan, this is one of the times that I really became aware of Dempster’s really fun and unique off the field personality. At this point in our conversation, Dempster pauses for a second before apologizing and saying that he just got distracted because his bench coach walked up with absolutely massive biceps. This comment cracks me up and then we get right back into things.

How does the feeling compare between what it is like to step out on the field for a game versus what it is like to step out to do stand up? Is one a lot more nerve wracking? 

He answers this question quickly saying that it is “way worse with stand up . . . I always felt prepared with baseball – I have been doing that my whole life.” He explains how intense it was do get out there and do stand up how it is “so bright I can only see the first row” and how hard it can be sometimes. Then he says “but that’s ok – you are just up there trying to get better . . . and the failures can teach you more sometimes than the success.

Well and on the field it’s not just you right, like you have your whole team behind you when you are pitching . . . so if you give up a big hit you can rely and hope your outfielders will help you out  . . . but onstage it is just you. Don’t worry he had mentioned giving up big hits or a grand slam before I did.

Ryan explains that someone told him once that you have to “test yourself and that if you aren’t going up there and bombing – you aren’t pushing the envelope enough.” He says that just because you don’t get laughs on something “it doesn’t necessarily mean you don’t have a good joke – it just means you need to work on it more. Tinker with it. The writing is such a big part of it.

Ryan explains that “the preparation part helps . . . that you can’t just go up there and wing it. Look at Jerry Seinfeld” he remarks – continuing on to explain how Seinfeld is probably one of the most prolific among comedians about writing things down and keeping track of his material. Then he cites Mitch Hedberg and the way he says it makes me think he wonders if I know about him and I laugh to myself a little remembering one of my college roommates who was absolutely obsessed with Hedberg and listened to his stuff non-stop. Dempster cites Hedberg for what he said about writing down his material: “If I think of something funny I write it down or if I don’t have a pen I convince myself it wasn’t that funny.

You mentioned writing and preparing. Preparing for baseball and preparing for stand up – are they as different as people think? Has your baseball background impacted your work and preparation in your comedy career? 

“It is the same as being a baseball player . . . I had to do the work and preparation behind the scenes to be ready for a game” he says – comparing that to the hard work and preparation that he puts into his work in comedy, before explaining that even with that preparation it is “still nerve wracking” to put his comedy out there. He talks then about how “there was a camera in his face for 20 years of my career [as a player]” and even with that he still goes out there feeling nerves on the comedy front.

Is there anything you would like fans to know about you that they might not? Feel free to take this question any way you want. 

He laughs and I tell him that I have had all kinds of answers from super serious personal moments to someone telling me they were doing a nude photo shoot during our interview. At the same time I was thinking, maybe I need to stop asking this question . . .

Hmm. Something fans don’t know about me. They might know about this, but probably not” he begins “But I was a practicing magician for five years – up close magic, slight of hand, coins, cards – that kind of thing. I got into it in A Ball because I had a pitching coach who was an offseason magician. He showed me something on the bus” and apparently Ryan was hooked: “I just started practicing . . . when people would be out there shagging balls I would be playing with my glove in the outfield and sometimes people would be like Ryan what are you doing. . .”

I guess one thing I have always heard is that you would do magic and fun stuff in the locker room hanging with your teammates . . .I was always goofing around” he explains before continuing to describe fondly having fun with things and how those moments with your teammates are so great.

After a great weekend at Innings Festival coming up – what do you have planned that you would like fans to know about?  What should we be looking for from you in 2020?

Well, I will continue to work with the MLB Network and then I will also be working with the Cubs new sports network.” Ryan explains that he will be bringing a talk show to the new Cubs Marquee Sports Network – they will be shooting six episodes in front of a live studio audience (likely starting in April) and he thinks they will begin to air soon after that. He suggests following @OffTheMound on Instagram to keep up with all the news.

Off The Mound_Boston 2020

Ryan will also be hosting a special edition of “Off The Mound” to benefit The Foundation To Be Named Later on April 3rd in Boston – during Red Sox opening day weekend. The special show will feature Pedro Martinez and Bronson Arroyo – who are teaming up with comedian Mike O’Malley “for a night of baseball, laughs, and entertainment for good causes.” The event will be held at Big Night Live and will raise money for FTBNL’s Peter Gammons College Scholarships. Tickets are on sale through for that event here.

Our interview ended with some really important (in my opinion) thoughts from Ryan on “Off The Mound” and why he does it: “I am excited to do this” he explains before going on “we dehumanize the athlete, we put them on a pedestal – I like to humanize them and appreciate them as people. Just because they have a bad game, or a bad night out on the ice, or give up a grand slam .  .  .” he describes the need and the importance for fans to see them as real people. “I enjoy bring the .  . . it is almost like we use social media to get up close with fans . . . this is similar” through the show we have a similar “way to get up close with fans.

Seriously everyone! As a baseball fan, “Off The Mound,” especially at Innings, is such a unique opportunity to be up close with baseball greats and to get to see their personalities – see them relaxed and chatting. Before we conclude I mentioned to Ryan how much fun I had last year and how cool it was to be in the crowd and have him call out that David Ross was out there too. Then I told him my ridiculous David Ross story – and props to him for patiently listening. But the point of that was, that moment I remember about David Ross cracking up the crowd when he yelled at these two preppy little fans who had been heckling him (while he wasn’t even playing in the game) isn’t a baseball memory – it’s a memory that showed that players are real people and that even while he was yelling Ross was having a good time with it and enjoying the fan interaction. That’s something we as fans don’t get to have often and Ryan Dempster has made that kind of fun banter and ability to get to know the players as people accessible to us as fans through “Off The Mound.”

Huge shoutout to Ryan Dempster and his team for giving us the opportunity to chat with him before the festival this weekend. (And credit to them for all the pictures in our article today)

I have gotten to interview a lot of musicians for Living The Fest Life – and that is cool, don’t get me wrong – but this was special for me as a baseball fan.

DON’T MISS OFF THE MOUND THIS WEEKEND! You never know who might be in the crowd next to you, who might sing, or who might show up on that stage.

Jake Peavy_Ryan Dempster_Innings Fest 2019

For more on Innings Fest – check out our 2019 Recap or visit the official website here.

For more on “Off The Mound” visit: www.OffTheMound.com or @OffTheMound on bothTwitter and Instagram.

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