The Chicago Cubs have been fodder for late-night talk-show hosts for decades, most notably during their record-setting 14-game losing streak at the start of the 1997 season.
“No one likes to be the brunt of jokes, the Jay Leno stuff,” then-Cubs manager Jim Riggleman said. “I haven’t seen it, but I’ve heard about it. But this is the situation we put ourselves in.”
The Cubs were often a joke — and the butt of many a joke. When Harry Caray appeared on “Late Night with David Letterman” in 1986, Letterman introduced a clip of Caray performing “Take Me Out to the Ball Game” during the seventh-inning stretch by saying: “If you happen to be at Wrigley Field and you can make it through seven innings of watching the Cubs …”
When your franchise is synonymous with losing, there’s not much you can do but wear it.
Stephen Colbert was fortunate enough to have started his stint as host of “The Late Show” 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.
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 “my three lucky Chicago Cubs” — Anthony Rizzo, Jake Arrieta and Kris Bryant — while yelling, “Woo!” like uberfan Ronnie “Woo-Woo” Wickers. The Cubs players acted visibly perturbed, showing off their acting skills.
Colbert, as you might have heard, is leaving CBS after the final “Late Show” Thursday night, ending the classic show that Letterman started in 1993 after leaving NBC’s “Late Night.”
The stable genius president with the world’s 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.
The last several months have been one long goodbye for Colbert, whose show will go down as another victim of Trump’s vengeance tour, even as Colbert no doubt will thrive elsewhere.
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’s comedy chops.
As a Northwestern graduate and Second City alumnus, Colbert attached himself to the Cubs, while admittedly not the world’s 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’s apartment near the ballpark and going to games during Ryne Sandberg’s heyday in the 1980s.
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’t from Chicago, you could tell it was dear to his heart.
That was the trip Colbert made to Wrigley to film a “Late Show” bit in which he played a hot dog vendor named “Donny Franks,” donning a costume and goofing with fans and players, including Rizzo, Kyle Schwarber and Carl Edwards Jr.
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 “Undercover Boss” in which Ricketts failed at several odd jobs at Wrigley, making him a perfect choice for a future role in the first Trump administration.
Colbert’s love of the Cubs didn’t preclude him from poking fun at the team. In 2022 he mocked first baseman Frank Schwindel’s stint as a relief pitcher in a lopsided game against the New York Yankees.
“I’m no baseball player,” Colbert joked. “And apparently neither is Frank Schwindel.”
The journeyman first baseman told Cubs beat writers, “I’d like to see him do it,” and facetiously challenged Colbert to face him at Wrigley. Colbert didn’t take him up on the offer, and when reminded during a trip to Wrigley in 2024 that he could’ve hit off Frank Schwindel, he replied, “A lot of people could.”
Colbert wasn’t the only late-night host to make the Cubs part of his shtick. Letterman in 1989 made a list of “Top Ten Chicago Cubs Excuses for Not Winning a World Series Since 1908,” which included: “Image of ‘lovable losers’ gets us more tail than Sinatra.”
Conan O’Brien, 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.
Like Colbert, O’Brien was a Cubs follower back in the day. You can watch a video on YouTube of O’Brien 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 and Old Town haunts this week, replicating O’Brien’s trip.
Why the Cubs? The 2024 White Sox lost a record 121 games, but do you remember any late-night jokes at their expense?
Maybe it’s easier to laugh at a team known as “lovable losers.” Sarcasm and the Cubs always have gone hand in hand.
“I’ve never had time for sarcasm,” Riggleman said in ’97. “It’s a cheap laugh. It’s very easy for people to use sarcasm. A lot of people use it … it’s their ‘shtick.’ There will always be a market for it, but that doesn’t mean I have to like it.”
When Leno made a trip to Wrigley to film a bit in 1988, when the Cubs were playing well, I asked if they were the most abused sports team in America by comics. He argued the Los Angeles Clippers and Indianapolis Colts were just as ridiculed at the time, but he said the Cubs always would be a good punchline because of their popularity.
“It’s a great team and everyone loves them,” Leno said. “That’s what makes it fun. It’s all good-natured, silly. It’s hard to make fun of people you really dislike because then it’s mean. It’s like a roast. Everybody knows the Cubs and you have that history, and that’s why it’s fun. Nobody gets ticked off.”
The end of the drought made the Cubs a more generic sports franchise, and the luckless Cleveland Browns are probably a more appropriate target for national ridicule these days.
But with outspoken talk-show hosts facing similar threats of cancellation, the days of mocking losing sports teams on late-night TV might soon be a thing of the past.
