Featuring the high-pitched vocals of Anthony Gourdine and a brace of solid material, Little Anthony & the Imperials had a much longer chart run than the majority of doo wop from the '50s. When the dust finally settled, the group clocked in with a total of ten entries in the Hot 100 between 1958 to 1974, including "Tears on My Pillow," "Two People in the World," "Wishful Thinking," "Oh Yeah," "So Much," "Shimmy Shimmy Ko Ko Bop" (not to be confused with the similarly titled "Shimmy Shimmy Ko Ko Wop" by the El Capris), "When You Wish Upon a Star," "Going Out of My Head," "Better Use Your Head," and "Hurt So Bad."

Gourdine formed the group in the mid-'50s after his previous group, the Duponts, disbanded. Grabbing friends Clarence Collins, Ernest Wright, Tracy Lord and Nat Rogers, the group was originally called the Chesters, but had their name changed to the Imperials by popular New York disc jockey Alan Freed. Gourdine's vocal similarities to the popular Frankie Lymon-inspired "kiddie group" sound, coupled with a tendency to chop up syllables and overstress lyrics, made theirs a style deceptively simple yet enduring. After revamping the group in 1964 down to a quartet (Lord and Rogers left, and Sammy Strain joined), the sound changed from doo wop to a harder, more uptown R&B sound, best exemplified on hits like "I'm on the Outside Looking In." Little Anthony decided to work as a solo artist in 1975, while Collins continued the act in Las Vegas for many years. Sammy Strain went on to great success as a member of the O'Jays, and Ernest Wright joined as one of the Platters and sang with the group Europa. For many lovers of the genre Little Anthony & the Imperials are simply New York styled doo wop at its smoothest and finest.

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