Songfacts®:

• Lewis wrote this song with his drummer Bill Gibson and his keyboard player Sean Hopper. The song pokes fun at the group's clean-cut image, as instead of getting tattoos, growing their hair and behaving badly, the band matured as they got more successful, which was only natural considering they were in their mid-30s at the time and more concerned with taking care of themselves than with enjoying the trappings of fame. The image issue became a problem, however, as the band was seen as conservative icons, especially after stirring performances of "The Star Spangled Banner" at the 1987 Major League Baseball All-Star Game and at the beginning of a concert video they released. Being labeled a Yuppie didn't suit Lewis, whose mother was an artist and father was a jazz drummer. Lewis hitchhiked through Europe when he finished high school, and smoked a lot of pot along the way. As part of the San Francisco music scene, they partook in plenty of borderline-illegal activities, but they were never big on the party scene. Said Lewis, "Everyone thinks I'm the boy next door because I look like the boy next door. But look at my parents, and look where I come from. I'm a beatnik kid."
• Members of the San Francisco 49ers football team, including Dwight Clark, Joe Montana and Ronnie Lott, sang the part near the end after Lewis says, "Tell 'em boys." For athletes, they did a pretty good job singing the "Here, there and everywhere, hip, hip, so hip to be square" vocals. Huey Lewis & the News are from San Francisco and were friends with the football players. Their paths would cross at different civic functions and charity events. On the Sports album cover, see if you can spot Dwight Clark making his famous catch.
• This song plays a role in the book and movie American Psycho, where shortly before killing Paul Allen, Patrick Bateman does a little monologue about Huey Lewis & the News, and says, "I think their undisputed masterpiece is 'Hip to Be Square,' a song so catchy, most people probably don't listen to the lyrics. But they should, because it's not just about the pleasures of conformity, and the importance of trends, it's also a personal statement about the band itself."
  
  Initial pressings of the movie's soundtrack included the song, which apparently was never negotiated. When Lewis found out, he refused to grant permission and about 100,000 copies of the album were recalled and destroyed. According to the bands manager at the time, Bob Brown, Lewis hadn't even seen the film, and his objection was over the brazen inclusion of his song on the album without his permission. "I think what they're trying to do is drum up publicity for themselves," Brown said.
• So how did the word "square" come to be a term for somebody not in with current trend or fashions? The term originated in African American slang and has been current from the 1940s. According to Brewer's Dictionary of Modern Phrase and Fable there are several suggestions for its origin, none of which are particularly convincing. One possible explanation the book gives is that the term derives from a jazz musician's and standard conductor's hand gesture that beats out a regular rhythm, the hand describing a square figure in the air.
• The music video was directed by the team of Kevin Godley and Lol Creme, who made some of the most innovative videos of the '80s, including "Rockit" by Herbie Hancock and "Every Breath You Take" by The Police. For the "Hip to Be Square" clip, they got a distinctive look by using a medical camera - the kind doctors use to see inside the human body. They had the band perform the song a few times a few feet away from the camera, and did the heavy lifting in post production - the band loved it because it was so easy for them. The resulting video contained angles previously unseen on MTV, including one from the point of view of the drumsticks. It was nominated for Best Experimental Video at the 1987 Video Music Awards.
• The band didn't put too much thought into their album titles. Fore! got its name because they like golf, and because it's their fourth album.
• In 2013, Huey Lewis did a parody of this song's American Psycho scene with Weird Al Yankovic in the role of Paul Allen, and Lewis as Patrick Bateman. Instead of discussing the song, Lewis talks about the movie, how it "works as a grim examination of male vanity, while also maintaining real genre thrills." When Lewis ax-murders Al, he declares, "try parodying one of my songs now, you stupid bastard." Al did a parody of the Huey Lewis & the News song "I Want A New Drug" called "I Want A New Duck."