When your franchise is synonymous with losing, there\u2019s not much you can do but wear it.<\/p>\n
Stephen Colbert was fortunate enough to have started his stint as host of \u201cThe Late Show\u201d on CBS when the Cubs began their renaissance in 2015, and he was part of a kinder, gentler skewering of the team during its championship run in 2016.<\/p>\n
It began that summer during a Cubs trip to play the Mets in New York, where he filmed a bit wearing Cubs clothing and rubbing up against \u201cmy three lucky Chicago Cubs\u201d \u2014 Anthony Rizzo, Jake Arrieta and Kris Bryant \u2014 while yelling, \u201cWoo!\u201d like uberfan Ronnie \u201cWoo-Woo\u201d Wickers<\/a>. The Cubs players acted visibly perturbed, showing off their acting skills.<\/p>\n Colbert, as you might have heard, is leaving CBS after the final \u201cLate Show\u201d<\/a> Thursday night, ending the classic show that Letterman started in 1993 after leaving NBC\u2019s \u201cLate Night.\u201d<\/p>\n The stable genius president with the world\u2019s thinnest skin apparently tired of getting mocked on a nightly basis by Colbert and his writers. So the network canceled the show after Colbert criticized its parent company for paying a $16 million settlement to President Donald Trump while it sought federal approval for an $8 billion merger with Skydance Media.<\/p>\n The last several months have been one long goodbye for Colbert, whose show will go down as another victim of Trump\u2019s vengeance tour, even as Colbert no doubt will thrive elsewhere.<\/p>\n Meanwhile, CBS will be one fewer place to turn to before hitting the sack, leaving fans of late-night TV to choose between Jimmy Kimmel and Jimmy Fallon, neither of whom has Colbert\u2019s comedy chops.<\/p>\n As a Northwestern graduate and Second City alumnus, Colbert attached himself to the Cubs, while admittedly not the world\u2019s biggest baseball fan. I sat with him for a few minutes in the dugout at Wrigley Field before a game one afternoon in 2016, and he talked about his former girlfriend\u2019s apartment near the ballpark and going to games during Ryne Sandberg\u2019s heyday in the 1980s.<\/p>\n He spoke fondly about places where he lived and establishments where he hung, from Wicker Park to Old Town to Rogers Park. Though he wasn\u2019t from Chicago, you could tell it was dear to his heart.<\/p>\n That was the trip Colbert made to Wrigley to film a \u201cLate Show\u201d bit in which he played a hot dog vendor named \u201cDonny Franks,\u201d donning a costume and goofing with fans and players, including Rizzo, Kyle Schwarber and Carl Edwards Jr.<\/p>\n He was filmed learning the ropes from the late hot dog vendor Rocco Caputo, who also taught Cubs co-owner Todd Ricketts during an episode of \u201cUndercover Boss\u201d<\/a> in which Ricketts failed at several odd jobs at Wrigley, making him a perfect choice for a future role in the first Trump administration.<\/p>\n Colbert\u2019s love of the Cubs didn\u2019t preclude him from poking fun at the team. In 2022 he mocked first baseman Frank Schwindel\u2019s stint as a relief pitcher in a lopsided game against the New York Yankees.<\/p>\n \u201cI\u2019m no baseball player,\u201d Colbert joked. \u201cAnd apparently neither is Frank Schwindel.\u201d<\/p>\n The journeyman first baseman told Cubs beat writers, \u201cI\u2019d like to see him do it,\u201d and facetiously challenged Colbert to face him at Wrigley. Colbert didn\u2019t take him up on the offer, and when reminded during a trip to Wrigley in 2024 that he could\u2019ve hit off Frank Schwindel, he replied, \u201cA lot of people could.\u201d<\/p>\n Colbert wasn\u2019t the only late-night host to make the Cubs part of his shtick. Letterman in 1989 made a list of \u201cTop Ten Chicago Cubs Excuses for Not Winning a World Series Since 1908,\u201d which included: \u201cImage of \u2018lovable losers\u2019 gets us more tail than Sinatra.\u201d<\/p>\n Conan O\u2019Brien, who in 1988 lived in an apartment near Wrigley Field with comedian Jeff Garlin, once proposed that the Cubs introduce a mascot named Hal Capone, based on the gangster Al Capone, to end their championship drought.<\/p>\n Like Colbert, O\u2019Brien was a Cubs follower back in the day. You can watch a video on YouTube<\/a> of O\u2019Brien and Garlin revisiting their old Wrigleyville pad and telling the occupant that Ernie Banks used to stop by between at-bats. Colbert visited his old Chicago apartment<\/a> and Old Town haunts this week, replicating O\u2019Brien\u2019s trip.<\/p>\n Why the Cubs? The 2024 White Sox lost a record 121 games, but do you remember any late-night jokes at their expense?<\/p>\n Maybe it\u2019s easier to laugh at a team known as \u201clovable losers.\u201d Sarcasm and the Cubs always have gone hand in hand.<\/p>\n![\"Comedian](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2026\/05\/CTC-COLBERT-05202-1.jpg\")
Comedian Stephen Colbert and Cubs pitcher Carl Edwards Jr. dance in the dugout during the taping of a skit before a game against the Brewers on Sept. 17, 2016, at Wrigley Field. (Nuccio DiNuzzo\/Chicago Tribune)<\/p>\n![\"Stephen](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2026\/05\/CTC-COLBERT-05203.jpg\")
Stephen Colbert sings \u201cTake Me Out to the Ball Game\u201d between innings during a Cubs game against the Blue Jays on Aug. 16, 2024, at Wrigley Field. (Tess Crowley\/Chicago Tribune)<\/p>\n