These posts are about the songs that just barely failed to cross the key line of chart success, entering the Billboard Top 40. Every song featured in this series peaked at number 41.

The Mann Act was cemented in U.S. federal law on June 25, 1910. Like most regulations with over a century of dust on it, the Mann Act has been amended and finessed over the years, but its core prohibition is against transporting women or girls across state lines for “immoral purposes.” In the most famous cases, the law has mostly been leveled against individuals who were lasciviousness preying on girls under the age of consent. As the nineteen-fifties came to a close, Chuck Berry became one of those individuals.

The rock ‘n’ roll trailblazer, who sang of a sixteen-year-old girl in tights dress, lipstick, and high heel shoes in one of his many hits, claimed that it was only the most innocent gainful employment he had in mind when Janice Norine Escalanti was brought by him from Mexico to the club he owned in St. Louis. Escalanti, who was two years younger than the subject of his hit single when Berry recruited her, offered a different interpretation of events. The courts sided with her. After an initial conviction was vacated because of the judge’s bigoted commentary from the bench, a retrial landed Berry a prison sentence. He served almost two years behind bars.

“Promised Land” was the first single from Berry following his release from prison. Borrowing the melody of folk standard “Wabash Cannonball,” the newly unconfined Berry offered a tale of a fellow who travels from Norfolk, Virginia to California by multiple means, with stops in Charlotte, Atlanta, Birmingham, New Orleans, and Houston (and Albuquerque apparently glimpsed from high above in an airplane). The performer was clearly agitated and feeling his freedom.

According to fellow rock ‘n’ roll founding father Carl Perkins, Berry came out a prison a deeply changed man, carrying around anger and bitterness that seemed to stick with him for the remainder of his life. The propensity for skeevy behavior lingered, too. Three decades after he was on the wrong side of the Mann Act, Berry got in trouble for secretly videotaping women as they used the bathroom on a property he owned. There’s no denying Berry’s importance in the foundation of rock ‘n’ roll, but there’s a big impediment to hero worship. His legacy should be as much about the ignominious behavior that no amount of guitar wizardry excuses.

Other entries in this series can be found by clicking on the “Top 40 Smash Near Misses” tag.