Liberty Vallance

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.