Derek Holland Is At It Again With His Harry Caray Impression, And He’s Bringing Ryan Dempster Along With Him

  • Jordan Rabinowitz

Baseball players are baseball players for a reason: they’re good at baseball. This doesn’t necessarily mean they’re good at other things, like doing impressions of other people, you know, because of all the time they spend playing baseball. Rangers starting pitchers Derek Holland and Ryan Dempster, however, moonlight pretty well as SNL-cast-member wannabees. Major League Baseball probably felt bad about all those times they unleashed their inner copyright douche when they ripped previous videos of the two funnymen off the web, so here’s a Fan Cave exclusive of Holland and Dempster doing their best Will Ferrell Harry Caray — color commenting on themselves.

The two have been doing Caray impressions long before they pitched on the same staff, so as expected, these are honed, well rehearsed and down to a T. But part of me feels like Ryan Dempster needs to sit out of the making-fun-of-Harry-Caray business for just a little while. Tasteful or not (which, all Harry Caray impressions are), maybe Ryan should wait a little longer before he starts teasing any aspect of his former club, the hapless Cubs.

But don’t worry North-Siders, he’s laughing with you, not at you. And plus, he and Derek are pretty spot on.