Watch Will Ferrell Bust Out His Hilarious Harry Caray Impression On Letterman

Will Ferrell is famous for his weird characters and over-the-top impressions. From Ron Burgundy to Robert Goulet, he’s made his living going larger than life, but even amidst those wacky personas, his take on departed Chicago Cubs announcer Harry Caray is particularly beloved. He aped the personality now and again on Saturday Night Live, and this week, he busted it out again for David Letterman…

It’s a testament to what a wild human being Harry Caray was that people still remember him fondly all these years later. He passed away back in 1998, but his legend still lives on, especially among Chicago Cubs fans who related to his brash honesty, unapologetic love of carousing and hard-drinking ways. In fact, he once went to the bars in Chicago 288 days in a row, hilariously keeping track of it all in an attempt to write those Budweisers off his taxes. No wonder he was nicknamed “The Mayor Of Rush Street”, the location of some of Chicago’s most iconic bars.

You can really tell how tuned in Ferrell is to the impression by how many clever references he makes. During the short segment seen above, he name-checks Chicago Cub greats like Greg Maddux, Rick Sutcliffe and Shawon Dunston. The comedian is a noted sports fan, and that really comes through, but then again, we should expect nothing less from Ferrell. He’s always been a guy who overprepares and really dives into each subject he teases. There’s no half-assing involved.

As for Caray, there’s currently a groundswell among Chicago Cubs fans to play a vintage clip of the announcer singing “Take Me Out To The Ballgame” during the 7th Inning Stretch. Right now, his legacy is honored through having guest conductors during every home game, but it would certainly be nice to see his smiling mug again.

In honor of Caray, order a Budweiser the next time you’re at a bar and root for the Cubbies. The better they do, the more likely we are to see Ferrell bust out this impression again.

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