Friday Five: Bank Robbers

This week’s Friday Five is inspired by a re-watching of the Keanu Reeves masterpiece Point Break; however, since there are no country songs about a gang of criminal surfers, we’ll just go with the bank robbing aspect. Here are my five favorite songs about bank robbers both real and fictional.

Honorable Mention: Ty Herndon’s single “Heather’s Wall” isn’t about a robber, but instead about a man bleeding to death on a bank floor after walking in on a robbery. But in the video, the robber is at least polite enough to apologize to poor Ty.

• 5. “The Famous Lefty Flynn’s” – The Grascals

  Boy, it sure is excellent when you’re cellmates with a famous bank robber and he dies in an escape attempt (after telling you where his giant stash o’ cash is located, of course). It’s like The Shawshank Redemption minus Morgan Freeman and plus some sweet banjo.

• 4. “Jesse James” – Bruce Springsteen

  There are several songs about infamous train and bank robber Jesse James, including an excellent one that’s been recorded by Roy Clark. My favorite song about the guy is on the Boss’ Pete Seeger tribute album We Shall Overcome. It’s less about James and his exploits than about the “dirty little coward” who shot him in the back.

• 3. “The Legend of Bonnie and Clyde” – Merle Haggard

  Haggard and his own Bonnie (Owens) wrote this single about the partners who “robbed and killed until both of them died;” it spent two weeks atop the country charts in ’68. If you can’t get enough of those Depression-era felons, that same year Flatt and Scruggs released a damn good album (with all of its song lyrics written by Tom T. Hall) about them called The Story of Bonnie and Clyde. The LP cover–which features Lester wielding a Tommy gun–is one of my favorites

• 2. “$100,000 In Pennies” – Bobby Bare

  When this song was recorded, a penny weighed 3.11 grams, which means the pennies the bank robber in this song hauled away would have weighed over 68,000 pounds. He may be spending his loot a penny at a time, but let’s hope he sets a few coins aside for hernia repair. A song this goofy and off-kilter could only have been penned by the fantastic Shel Silverstein.

• 1. “Pretty Boy Floyd” – Woody Guthrie

  On this song–which has been covered by many a singer–Guthrie romanticizes the Depression-era bank robber and Oklahoman folk hero as a Robin Hood type who stuck it to those men who robbed with a fountain pen.