Tonight’s episode of The Late Show seems up to be an exciting one, as host Stephen Colbert (The Colbert Report, The Daily Show) with this Thursday’s guest and former host David Letterman (My Next Guest Needs No Introduction with David Letterman, Everybody Loves Raymond) were spotted yesterday afternoon, seemingly dropping items off of the rooftop of a building nearby the Ed Sullivan Theater, the show’s taping studio. The moment was caught by Bluesky user Carolyn Petit (@carolynmichelle.bsky.social), featuring a blue upholstered chair mid-drop from a rooftop where Colbert and Letterman can be seen watching on.

See the post below, via Bluesky.

Holy shit y’all this is not a drill, David Letterman and Stephen Colbert are dropping stuff off the rooftop of a building near the Ed Sullivan Theater!

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— Carolyn Petit (@carolynmichelle.bsky.social) May 13, 2026 at 2:04 PM

Some are speculating that the chair is a part of the show’s set, due to its resemblance to the guest chairs used on The Late Show. Letterman, as pictured, will appear on tonight’s episode as a guest; Letterman had previously hosted Late Night With David Letterman on NBC from 1982 to 1993, then moved to hosting The Late Show on CBS until his retirement and passing of the mantle to Colbert in May 2015. He has since been a vocal supporter of Colbert’s success as a late-night host and critic of CBS’s decision to cancel the show.

Here, dropping stuff off a rooftop may be a reference to a former segment of Letterman’s from his Late Night hosting days – One of his career’s most popular recurring bits was when he would drop miscellaneous items off of a five-story tower, often taking object requests from street interviews. 

While nothing has been confirmed so far, Letterman’s episode will air tonight, which has audiences wondering whether or not this throwback will make an appearance in the episode.

This Thursday rounds off The Late Show’s penultimate week, entering the final four days up to the established finale date of May 21. Previously this week, Colbert hosted late-night TV hosts Jimmy Kimmel (Jimmy Kimmel Live!, The Man Show), alongside HBO’s John Oliver (Last Week Tonight with John Oliver, The Daily Show with Jon Stewart) and NBC’s Seth Meyers (Saturday Night Live, Late Night with Seth Meyers) and Jimmy Fallon (Saturday Night Live, The Tonight Show Starring Jimmy Fallon) in a reunion of the Strike Force Five; Tom Hanks (Saving Private Ryan, Forrest Gump), Julia Louis-Dreyfus (Seinfeld, Veep), and Pedro Pascal (Game of Thrones, The Last of Us). Segments from this week included former U.S. President Barack Obama for a “Colbert Questionert,” and a Broadway performance medley featuring Annaleigh Ashford (Bad Education, Unbelievable), Patrick Wilson (The Conjuring, Insidious), Ben Platt (Pitch Perfect, The Politician), Christopher Jackson (Moana, Bull), and Bernadette Peters (The Good Fight, High Desert). 

mxdwn reported prior that Kimmel would not tape or air a new episode on May 21, instead airing a rerun out of deference to Colbert’s send off.