Tim Dillard: Baseball’s Funniest Man

Tim Dillard isn’t your average minor league relief pitcher. It’s not the wild hair, the lumberjack beard, or the wacky side-arm delivery that sets him apart from his peers. Nor is it the fact that he has survived fourteen years in professional baseball despite being a 32nd-round pick from a tiny community college with a name as hard to pronounce as it is to find on a map. It’s not even the fact that Dillard found himself a job in 2016 pitching for the Colorado Springs Sky Sox (Triple-A affiliate of the Milwaukee Brewers) by showing up at baseball’s Winter Meetings uninvited with homemade business cards that simply stated “Tim Dillard-RHP” and handing them to any and every baseball executive who walked by.

No, there’s nothing average about Tim Dillard. Even if he openly calls himself a Four-A pitcher, the designation given to players who spend their career somewhere in the frustrating crossroads between the major and minor leagues, Dillard will never be defined just by his statistics on the field. And it’s a good thing for fans. If they viewed Dillard simply as a ballplayer, just another uniform number in their program, they would miss one important fact.

Tim Dillard is the funniest man in baseball.

Dillard’s near-cult following among fans has been growing for years, fueled by his impersonations of baseball analyst Tim Kurkjian on ESPN, his Will Ferrell-esque Harry Caray routine, and his honest and hilarious blog about day-to-day life in the minor leagues. Within the last year his online notoriety has burgeoned thanks to his discovery of Dubsmash, a cell-phone app that pairs a 10-second video recorded by the user with audio from a popular movie, song, or celebrity.

“Last season in Colorado Springs, I was goofing off in the clubhouse, and one of our relievers Brent Leach casually said, ‘I’m surprised you don’t Dubsmash.’ Within 24-hours, I had done nearly 30 of them.”

Since then, Dillard has released a steady stream of videos re-enacting his favorite movie scenes on his Twitter account (@dimtillard). Although the ballpark is his workplace, it has also become his playground, the majority of his videos being filmed in the clubhouse, dugout, or right on the field itself. It hasn’t just been baseball fans who enjoy Dillard’s videos.

“My teammates have been awesome. Some are ‘too cool for school’ at first because they don’t quite get the point. But once they see some of the videos and the process, they start coming up with their own ideas. The coaches didn’t quite understand early last year.  They see it as playing video games, playing cards, board games—basically as team camaraderie. Now, I have several in the organization following me on Twitter and Instagram and throwing out suggestions.”

Dillard frequently incorporates his teammates, coaches, and other team employees in his videos. He praises some of his teammate’s acting skills—Brent Suter for his re-occurring role as a raptor in Jurassic World videos, Jaye Chapman for his ability to play “the strong female character”, and Jake Elmore, who Dillard says could have a legitimate acting career following his playing days—but refuses to dish on which teammates are poor actors.

“If I call anyone out, they wouldn’t participate anymore!”

Dillard and his Sky Sox teammates plan and record the videos around team meetings, practices, and games, filming the scenes in different locations in and around the ballpark. In one, pitcher Jim Miller and outfielder Shane Peterson kung-fu fight in front of their lockers. Another shows Dillard and Miller playing air guitar to the tune of the Brooks & Dunn hit My Maria on top of the dugout. Dillard does scenes from The Office in his manager’s actual office, Jurassic Park re-makes in the outfield grass, and Willy Wonka outtakes in the weight room. The videos offer fans a behind-the-scenes look into the lighter side of professional baseball. But, especially in light of recent clubhouse drama in the NBA caused by a locker room video, Dillard understands the risks inherent in recording the antics of his teammates.

“I seek advice and discernment from people who have good judgment if I think something is inappropriate or controversial. We make sure nothing that should be kept private is made public. But we keep it fun and light and don’t take ourselves too seriously. At least, I don’t.”

As more and more fans tune into his videos, Dillard dreams bigger and bigger. His videos have become more complicated, often involving multiple teammates, costumes, and props. He hopes to film a scene with the whole team, grounds grew, and front office involved. He has even started to think about how he could capitalize on his successful comedy when his baseball career ends.

“When I’m done playing at age 45, I’m hoping I can turn my pointless fun into some sort of occupation earning a paycheck. I respect the broadcasting world immensely. If there’s an opportunity in that field, I’d seriously consider it. I’ve been really encouraged to do radio when I retire—some teammates even say I have a face for it!”

For now, Dillard is happy being a full-time baseball player and father and a part-time comedian.

“Thankfully, I keep getting a job playing baseball which is and will always be the dream job.”

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