Stephen Colbert's Legacy: From Cubs Jokes to Late-Night Comedy (2026)

Stephen Colbert's departure from The Late Show marks the end of an era for late-night comedy, and his relationship with the Chicago Cubs is a fascinating chapter in that story. Colbert's love for the Cubs, coupled with his comedic talent, created a unique dynamic that entertained audiences and showcased the team's enduring legacy. The Cubs, a franchise synonymous with losing, have long been a punchline for late-night hosts, but Colbert's approach was different. He embraced the team's history and charm, turning their reputation into a source of humor and connection with fans.

Colbert's journey with the Cubs began in 2015, as the team embarked on a remarkable renaissance. He found a kindred spirit in the Cubs' players, particularly Anthony Rizzo, Jake Arrieta, and Kris Bryant, who playfully endured his antics. One memorable moment was Colbert's portrayal of a hot dog vendor, Donny Franks, at Wrigley Field, where he interacted with fans and players, including Rizzo, Kyle Schwarber, and Carl Edwards Jr. This bit showcased Colbert's ability to blend humor with his genuine appreciation for the team and its history.

His love for the Cubs extended beyond the field. Colbert's visits to Wrigley Field and his interactions with the city's culture, such as his time in Wicker Park, Old Town, and Rogers Park, revealed a deep connection to Chicago. This personal connection added a layer of authenticity to his humor, making it more than just jokes about a losing team.

However, Colbert's comedic style also included playful mockery of the Cubs. In 2022, he joked about Frank Schwindel's brief stint as a relief pitcher, highlighting the team's unique challenges. This light-hearted ribbing was a part of the Cubs' charm, as it played into the team's self-deprecating nature and the fans' acceptance of their losing streak.

The Cubs' reputation as 'lovable losers' is a significant factor in their enduring appeal to late-night hosts. As Jim Riggleman, a former Cubs manager, noted, sarcasm and the Cubs have always gone hand in hand. The team's popularity and history make them an easy target for humor, but it also allows for good-natured and silly jokes that don't offend fans. This dynamic is a delicate balance, as Colbert's approach demonstrates.

Colbert's departure from The Late Show is a loss for late-night comedy, but it also highlights the changing landscape of entertainment. With the rise of outspoken talk-show hosts and the potential for cancellation, the days of mocking losing sports teams on late-night TV might be evolving. The Cubs, once a staple of late-night humor, may now be a more generic sports franchise, but their legacy as a 'lovable loser' team remains. The team's ability to embrace their reputation and turn it into a source of entertainment is a testament to their resilience and the power of humor in sports.

In conclusion, Stephen Colbert's relationship with the Chicago Cubs is a fascinating blend of personal connection, comedic talent, and the team's unique history. His departure from The Late Show leaves a void in late-night comedy, but the Cubs' legacy as a 'lovable loser' team continues to entertain and inspire, reminding us that sometimes, it's the losing that makes the laughter the most meaningful.

Stephen Colbert's Legacy: From Cubs Jokes to Late-Night Comedy (2026)

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