Tonight marks the finale of the long-running Comedy Central show The Colbert Report, and Stephen Colbert will retire his character “Stephen Colbert” as he prepares to take over The Late Show from David Letterman.

Over the last nine years, Colbert and his persona have had their share of memorable moments: “Better Know”ing more than eighty members of Congress (including Jan Schakowsky and Mike Quigley), adopting an eagle, having a Ben and Jerry’s ice cream flavor named in his honor, sponsoring the US Speedskating team during the Vancouver Games, launching a SuperPac, and creating the word “truthiness.” The Peabody and Emmy winning show has also encountered some controversy, whether it was the host's infamous roast of George Bush at the 2006 White House Correspondents Dinner or a sketch about Washington’s football team and the subsequent tweet that resulted in the #CancelColbert campaign led by Chicagoan Suey Park.

Although we can be disappointed that Colbert never made it to Chicago for a show (one can dream about a Colbert Late Show in Chicago, a la Jimmy Fallon), his roots here run deep. He came of age in Northwestern’s storied theater department and then honed his chops at Second City. Here are a handful of segments and interviews with some of the city’s best and brightest.

Chicago Tries for the Olympics

Ah, December 2009, when our local politicians (plus Oprah) took the Chicago road show to Copenhagen for a chance at the 2016 Olympic Games. After an overview of the civic platitudes and nicknames, and Colbert fondly recalls his fictive days as a shock jock on “The Z96 Morning Asylum with Stevie C and Dr. Dave.” Then Stephen and George Wendt down Old Style and trash talk Tokyo, Rio, and Madrid.

The Sun-Times Fires Its Photographers

When the Chicago Sun-Times made national headlines firing their entire photography staff and recommended that reporters instead use their iPhone cameras, Colbert did his best to give the staff photographers “the Colbert Bump” and pondered what the pros and cons of professional photographers and iPhone photographers. Check out the cameo by Tribune media columnist Robert Feder.

Jeff Tweedy Shows Up

A few days before 2008 election, Colbert sat down with Jeff Tweedy for the first time. Although Tweedy would go on to appear on the show with Mavis Staples and his son Spencer, this interview in particular is Colbert being “Stephen Colbert” at his finest. Colbert asked Tweedy if he was a socialist for giving away free music on the band’s website (it was 2008), and Tweedy laughs, “we’re just really lousy capitalists.” Colbert also tried to match Tweedy’s “low-key” attitude. Six years later, Tweedy and son Spencer returned to the Report to sing their song, “Low Key.”

Stephen Colbert vs. Rahm Emanuel

After the early successes of the “Better Know a District” segment, where Colbert stroked the mustache of a Georgia Congressman and he got a Florida Congressman running unopposed to say, “I enjoy cocaine because it’s a fun thing to do,” then-Congressman Rahm Emanuel told newly elected Democratic representatives to avoid appearing on The Colbert Report. The result? An unresolved feud with a seven-year hostage crisis—Colbert claims to have…the missing tip of Rahm’s finger. Colbert did eventually announce his willingness to trade it back in exchange for appointment to the position of White House dog, although Rahm has made it clear that he refuses to negotiate with pundits.

Theaster Gates: Cult Leader

Theaster Gates sat down with Stephen earlier this year to talk about the ReBuild Foundation and his artwork. Stephen was a bit baffled by Gates’ work though. “What worries me about your work,” Colbert said, “is that you’re turning things into art that I used to not have to think about. I’ve never gone up to a house or seen a house before and said ‘I’m not sure I get this house,’ the way I don’t get some art.” The interview’s immortal question, however: “Theaster, are you a cult leader?”