Tuesday night’s Late Show was the penultimate episode, so naturally it featured two big stars: Bill Murray and Bob Dylan. Both have a long history with Letterman: Murray was Letterman’s first Late Night guest back in 1982, and Dylan first performed on Late Night in 1984.
The second-to-last show was weird and funny and sweet (both figuratively and literally). After Murray popped out of a cake for his interview, Bob Dylan performed the melancholy jazz standard “The Night We Called It a Day” from his album of Sinatra covers, Shadows in the Night. Dylan and Sinatra aren’t obvious bedfellows, but Dylan’s Letterman performance will show you why Sharan Shetty called the album “a lovely, idiosyncratic tribute to a bygone era.” The song was the perfect way to say goodbye to a titan of late night.