The segment was taped on Thursday, October 7,as Regis accompanied Pee-wee (aka Paul Reubens), who spent the day getting acquainted with New York City by sightseeing and checking in to Foursquare on all his stops along the way to launch his Pee-wee Herman Foursquare Badge.
His stops included The Apple Store at 5th Avenue and 59th Street, Jacob the Jeweler at 48 E. 57th Street, 4 Food at 286 Madison Avenue, and Times Square's TKTS Booth.
Herman's last stop was the Stephen Sondheim Theatre at 124 W. 43rd Street, where his Broadway show, The Pee-wee Herman Show, will begin previews on October 26 with and official opening on November 11.
Based on the Saturday morning television show that became a cultural phenomenon, The Pee-wee Herman Show is an all new celebration of sophisticated silliness. Alex Timbers will direct the production, which co-stars original Pee-wee Herman Show cast members John Moody, John Paragon, and Lynne Marie Stewart, along with Jesse Garcia, Phil LaMarr, Josh Meyers, Drew Powell, and Lance Roberts.