From Benton Harbor, MI (about 60 miles from Chicago), the Five Emprees had a big hit in Chicago in 1965 with "Little Miss Sad," a cover of a song originally released (and written) by the Addrisi Brothers. Driven by an infectious ascending riff, close British Invasion-influenced harmonies, and the kind of Trini Lopez-influenced rhythm that Neil Diamond would popularize on songs like "Cherry, Cherry," "Little Miss Sad" also had some success in a few other regions, and made number 74 on the national Billboard charts. Most of the Five Emprees' scant recorded repertoire leaned heavily on cover versions, however, and they never repeated the success of "Little Miss Sad," despite recording an album and several follow-up singles through 1968.
The Five Emprees originally formed in high school as "Cook and the Chefs" (named after singer Don Cook), changing their name to the Impressions and then the Five Empressions before getting a contract with the small Chicago indie label Freeport Records. Although "Little Miss Sad" was originally released under the name the Five Empressions, it was quickly changed after the famous soul group the Impressions got an injunction against them. Though originally issued as the B-side of the Debbie Dovale cover "Hey Lover" (co-written by Don Covay), it was "Little Miss Sad" that saw chart action, motivating an album (also called Little Miss Sad) in late 1965 that was filled out by hastily recorded and rather poorly produced cover versions, many of the songs dating from the pre-Beatles era. The group did release a few more singles in 1966-68 on various labels, most of which were covers of obscure pop/rock and soul songs done in a passable but callow British Invasion harmony-influenced manner betraying their young age (all but one were still teenagers when they began recording). For their final releases, they moved toward a soul-rock sound with horns, and although they hung around until the early 1970s, they didn't release anything after 1968. Their Little Miss Sad album was reissued by Arf! Arf! on CD in 2004, with the addition of numerous bonus tracks from non-LP singles and unreleased outtakes.