“It Hurts Me” – Bobby Sherman (1965)

Teen idol tenderness meets classic heartbreak balladry.

Before his late-‘60s TV stardom and bubblegum pop hits, Bobby Sherman released a lesser-known but emotionally rich ballad that offered a glimpse of his potential beyond poster-boy charm. “It Hurts Me,” penned by veteran songwriter Dick Glasser, was the B-side to the upbeat “You Make Me Happy,” yet it arguably carried more emotional weight and staying power.

Where the A-side leaned on bright harmonies and teen-centric optimism, “It Hurts Me” slowed things down, trading pep for pathos. A sparse arrangement of piano and guitar lets Sherman’s voice take center stage — plaintive, sincere, and aching with unspoken heartbreak. The production is modest but intimate, reminiscent of the era’s masters of melancholy like Gene Pitney or Roy Orbison.

Glasser, who had a sharp eye for the teen market, clearly wrote the song to showcase Sherman’s emotional range. He recognized that in a pop landscape filled with clean-cut crooners, depth could set a heartthrob apart. “It Hurts Me” taps into universal adolescent heartbreak — the kind of aching sincerity that dominated mid-‘60s radio and made teen girls clutch 45s to their chest like diary entries.

Decca Records likely hoped Sherman could ride the wave of emotional balladry that had made stars out of other young male vocalists. With his boy-next-door looks and vulnerable delivery, Sherman fit the mold — but “It Hurts Me” also hinted at an artist capable of more than just catchy teen tunes.

Though it never became a breakout hit, “It Hurts Me” remains a poignant relic from an era when heartbreak was king, and sincerity was currency in pop music.

Soft, sorrowful, and strikingly real — a forgotten gem that still sting