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"Hip to Be Square" is a song by Huey Lewis and the News, written by Bill Gibson, Sean Hopper, and Huey Lewis, and released in 1986 as the second single from the multi-platinum album Fore!

The song features San Francisco 49ers players Joe Montana, Ronnie Lott, Dwight Clark, and Riki Ellison singing backup vocals. The single reached number three on the Billboard Hot 100.

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 an endoscope, 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.

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." The song was originally featured on the accompanying soundtrack, but shortly after it was released, the album was pulled from the shelves and the song was removed before being reissued, but a small number had already been sold. Reports erroneously claimed that Lewis had objected to the context in which his song was used in the film and demanded it be removed from the album. In reality, the film's production team had paid for the rights to use the song in the film, but overlooked receiving the rights to include it on the soundtrack. When the soundtrack was released with the song on it, Lewis had it withdrawn, as the soundtrack rights had not been secured.

In 2013, Lewis himself guest starred in a parody of the scene with "Weird Al" Yankovic for comedy website Funny or Die.

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."