From his well-known practical jokes to his deadpan humor, Cubs closer Ryan Dempster is the kind of guy who is always one step ahead of you. In the course of a conversation, you can never be sure if he’s telling the truth or pulling your leg.

Whether it’s giving the play-by-play of an off-season shuffleboard tournament with the elderly or explaining Glendon Rusch’s penchant for clubhouse magazine subscriptions, it’s tough to distinguish between reality and raillery.

In this interview, Dempster tells all about his famous pranks, his big three-year contract and his high hopes for the future of the Cubs.

The Heckler: You’re portrayed as a really funny guy who’s always cracking jokes. Is that an accurate depiction?
Ryan Dempster: I think that’s pretty accurate. I don’t know if I’m necessarily funny, but I’m always cracking jokes and playing practical jokes. That’s what I like to do—make these guys laugh, keep them loose.

TH: Paul Sullivan from the Tribune said you’re “always available and frequently hilarious.” Does your reputation as being a decent, approachable guy make you a magnet for overzealous Cubs fans?
RD: It’s more like “frequently available and always hilarious”—I think there’s some sort of typo there. I always like to be available. I don’t like to dodge questions. The media has their job to do and part of our job is being available for them. I think it makes me approachable—I’m very outgoing with fans. If I’m out in a restaurant, I don’t mind being approached by people, but if I’m shoving a forkful of pasta in my mouth, I don’t want someone coming over and asking for an autograph. I do like that every time I go to a bar they buy me drinks. I hope they continue to do that.

TH: You do a pretty solid Harry Caray impersonation. Do you do any others?
RD: I loved Harry Caray. I always thought he was so funny, and then as I got older, I found out he was mostly drunk.  I don’t know about impressions—maybe it’s more quoting movie lines that’s my forte. “Tommy Boy,” “Dumb and Dummer,” “Black Sheep,” “Anchor Man”—I could sit down and quote the whole movie. I can quote the whole movie “UHF” starring Weird Al Yankovic.

TH: Besides you, who is the funniest guy on the team?
RD: Glendon Rusch. He makes me laugh every single day. When we were in the bullpen together it was just a blast. It’s not only that he has great, smart wit. He’s just one of those funny guys. All year, he took magazine flyers and sent them in and at end of year, we had tons of magazines—People, Us Weekly, Cosmo—all of these magazines delivered in his name to the clubhouse.

TH: There was a clip of you pranking Will Ohman. You had the tires removed from his SUV and then scattered them around the spring training facility. Has Will gotten you back for that?
RD: He got me first. He put eyeblack in my hat and superglued my clothes. I got him really good so he doesn’t even think about getting me back. He appreciates good humor.

TH: Was that your best prank ever?
RD: That one was pretty good. Whoever tries to get me next, I’m going to take out a billboard ad near Wrigley and put up their home number, cell number and picture that says ‘call me anytime.’ That’s going to be my next one.

TH: Have you ever had any pranks go wrong? 
RD: I’m usually pretty thorough. One time I was on a golf trip with Kevin Millar, Mark Sweeney and Steve Lyons and Mark and Kevin messed with my room a little bit. We had adjoining rooms. I went out the back window of the bathroom and took every single piece of furniture in Kevin’s room and moved it to his patio, all just like he had left it. I moved his entire bedroom out there. But he caught me as I was going out the door–I had to stay in my room all night [for fear of retaliation].

When I was at the [Cincinnati] Reds, I wore a Barry Larkin jersey and people actually asked me, “Barry, can you sign this baseball card?” I don’t know if they noticed, but I’m white and he’s black. It was funny. He loved it. He thought it was the greatest.

TH: Once and for all, do you go streaking at least three times a week?
RD: No, that’s purely a myth. Well, three times a week is. Yes, I did go streaking before. I have not gone streaking this year. Last season, during the season, technically I wasn’t streaking–I served cookies in an apron, only an apron.

TH: Last year you did a regular appearance on Mike North’s morning show. How’d you get a word in?
RD: It’s funny. Any time I’m asked questions by the media, whether it’s TV, newspaper, or radio, they always want your opinion, unless it differs with theirs. Then they have a problem with it and then they want to write a bad article about you. Mike and I have a great relationship. I just wanted him to see what a player’s view is. We disagree on some things. I just have to keep talking or Mike will just jump in there and you’ll never get a word in.

TH: A lot of people are pretty down on Dusty. What do you think about that?
RD: I think he’s one of the best guys to have ever managed baseball. I think the reason they are [down on him] is because, number one, he put the blame on himself. I can’t honestly remember one time that Dusty has sat there and blamed a player. He always takes the blame himself. He gives us all the positive feedback we can get. Corey [Patterson] had a really tough year and Dusty, all the way down to the end, stood behind him. He sticks behind his players. It hurts to lose for you and your fans, but it also hurts to lose because your manager is such a great guy.

Everyone’s going to understand what a great manager he is after this year.

TH: You signed a pretty big three-year contract heading into this season. Does this change your perspective as a player? Do you think it changes fans’ expectations for you?
RD: I don’t know what their expectations are of me. I know what my expectations are of myself and I’m pretty sure not a lot of people are going to have higher ones. I just want to continue to do the same job I did last year. I just hope my teammates don’t expect me to pay for more dinners because I’m making more money.

TH: You’ve been known to take a bike to the stadium. Now that you’re making more money, are you going to upgrade?
RD: I used to until someone stole it. I want to get a motorized cart but I’m scared that the AARP is going to break down my door. I might get a golf cart.

TH: Wouldn’t driving a golf cart to the stadium be illegal?
RD: It’s only illegal if you get caught.

TH: How does having a champion on the South Side affect the way the Cubs approach the new season?
RD: I hope it doesn’t change our attitude. Let’s face it: We understand the pressure is going to be just as huge for us to win a World Series. But at same time, we really want fans to understand and to know that we want nothing more than to win a World Series and have a parade twice as big. If we win the World Series, I’ll throw my credit card down and it’s open bar for anyone who wants to stop and have a drink.  But, we’re going to need help. We’re big boys and we’re getting paid, and we understand that booing is part of the game, but at the same time, we’re humans. We’re not robots. Why do guys get into streaks when they can’t get a hit? Because they’re confidence is way down. I just fear that the first game we lose we’re going to get booed. If we’re continually going out there and messing up, go ahead, we deserve it.  But I remember last year, fans booed Derrek Lee. Are you kidding me? The guy led the Major Leagues in hitting. How does he get booed. It’s not that we’re not big boys and can’t deal with it—booing is part of the game—but you’d be surprised how much it helps with little pat on the back. As for the other team, boo the hell out of them.

TH: What gives you hope that 2006 will be different than the last couple of seasons for the Cubs?
RD: Health. Everybody’s healthy. We have a great leadoff guy in Juan Pierre, bullpen help. And just the drive we have. It’s not fun to sit on your couch and watch other teams play.

From the January 2006 issue.