“Hip To Be Square” is from Huey Lewis and the News’ 1986 album “Fore!” and peaked at #3 on the Billboard Hot 100. According to Huey, the song was meant to be ironic and was originally written in third person; it wasn’t intended to be an anthem for square people, and the irony was mostly lost in translation to listeners. Lewis considers the misconstrued message one of his regrets in his career. The video is super fun and features Pro Football Hall of Famers, Joe Montana and Ronnie Lott singing back-up vocals.