The Providence, RI native joined funk group L.T.D. as a drummer and co-lead vocalist (Richie was originally The Commodores’ saxophonist and co-lead vocalist.) The band initially scored hits with more of a funk-based sound (like the Top 10 smash “Every Time I Turn Around (Back In Love Again)” before becoming better known for slightly sappy ballads almost exclusively featuring Osborne on lead (“Love Ballad”, “Where Did We Go Wrong” and the haunting “Stranger”.) Finally, in 1982 (the same year Richie departed The Commodores,) Osborne split L.T.D. and started his solo career.
His ratio of uptempo tracks to ballads was probably a bit more even than Richie’s was, but Jeffrey’s most fondly remembered songs are still sentimental slow jams-1983’s dramatic “On The Wings Of Love,” and what would end up being his biggest solo hit, “You Should Be Mine (The Woo Woo Song).” This seductive midtempo jam provided some much needed chillout time during the summer of 1986…a time period that was dominated by danceable jams from Janet Jackson, Madonna and the Timex Social Club. It is, of course, best known for Osborne’s chanting of the words “woo woo woo” following the chorus. However, that parenthetical title is a bit misleading. Many people think he’s asking “can you woo woo woo?,” but in reality, he’s saying “and you should be mine”-he’s just stretching the word “you” into four syllables. And you thought that sort of thing started with Whitney (“and iiiii-e-iiiii-e-iiii will always love yoou-oooouuuu!”
The video itself is pretty standard Eighties fare, which means there are a couple of interesting/cheesy/embarrassing things to note. One is the video plot: black man leaves Halle Berry lookalike for blonde. In today’s era of heightened sensitivity, do you think that would go over without sistas everywhere going into a tizzy? While this is happening, Jeffrey spends much of the video working on his Taylor Swift Surprised Face (patent pending) or working the forlorn look, an expression that suggests he was correct to not go into acting. Jeffrey’s also performing with a full band in this video despite the blatantly obvious fact that 85% of the song was recorded on a synthesizer. Finally, the marquee where Jeffrey’s name is placed looks like the Soul Train Scramble Board. Did the video director place a last second call to Don Cornelius?
After “You Should Be Mine” peaked at #13 on the pop charts, it looked like Jeffrey was about to make a huge pop breakthrough. Unfortunately, it didn’t materialize. He recorded a duet with Dionne Warwick the following year that peaked at #12, and he never scored a pop top 40 hit after that. His golden pipes remain in high demand, however, and you can bet that wherever he plays, someone asks him to “woo woo woo.”