Gene Pitney

One of the most interesting and difficult-to-categorize singers in '60s pop, Gene Pitney had a long run of hits distinguished by his pained, one-of-a-kind melodramatic wail. Pitney is sometimes characterized (or dismissed) as a shallow teen idol-type prone to operatic ballads. It's true that some of his biggest hits -- "Town Without Pity," "Only Love Can Break a Heart," "I'm Gonna Be Strong," "It Hurts to Be in Love," and "Twenty Four Hours From Tulsa" -- are archetypes of adolescent or just-post-adolescent agony, characterized by longing and not a little self-pity. But Pitney was not just an archetype of his style -- he was one of the best at his style, and indeed one of the few (along with Roy Orbison) that could pull it off convincingly. Also (like Orbison), he had more range than he's generally given credit for, making forays into tough pop/rock, country, and even borderline rockabilly. Other than Dionne Warwick, he was the best interpreter of Bacharach-David's early compositions. Although he didn't pen much of his material, he was a composer of note, writing "He's a Rebel" for the Crystals, and "Hello Mary Lou" for Rick Nelson. He was also something of a closet hipster -- he was the first American artist to cover a Jagger-Richards song ("That Girl Belongs to Yesterday," which was a British hit before the Rolling Stones had ever entered the U.S. Top 100), contributed to an actual Rolling Stones session in early 1964 (during which they recorded "Not Fade Away"), had a brief fling with a teenage Marianne Faithfull, and recorded songs by Randy Newman and Al Kooper long before those musicians became famous. Pitney broke into the music as a songwriter in his late teens, getting his first taste of success when Rick Nelson had a hit with "Hello Mary Lou" in 1961. That same...