Will Ferrell Impersonates Cubs Announcer Harry Caray On ‘The Late Show’

This is definitely a joke that went over a lot of people’s heads. Will Ferrell showed up during David Letterman’s last few episodes on The Late Show as one of his classic characters, the late Cubs commentator Harry Caray.

Caray was a longtime baseball announcer, who was famous for his 80s/90s time with the Cubs, singing “Take Me Out to the Ball Game” during the seventh inning stretch and his very strong personality.

In the clip, Ferrell’s Caray is sitting in the audience, senile, discussing the Cubs’ chances this season with [Greg] Maddux and [Rick] Sutcliffe leading their rotation: to put this in perspective, the two pitchers were last in the Cubs’ rotation together during the 1991 season.

And after the two shared a bit of banter, where Ferrell’s Carey called Letterman by the wrong, he left while singing his famous Cubs rendition of “Take Me Out to the Ball Game.”