Boy George is, was and always will be a soul singer (direct precedent: Smokey), so partnering him with Teddy Riley for a couple songs on 1989’s High Hat was a masterstroke on behalf of George’s American record company (although they had no motive in mind other than making a hit, which is kinda what record companies are known for so why am I even mentioning this?) Anyway, Riley and Gene Griffin (who was less a musical talent and more of a proto-Suge Knight) did two records for George: one of which I can’t recall (days later, I remember it; it was called “Whether They Like It Or Not”, and it was OK). The other was “Don’t Take My Mind On A Trip”, a jamming slice of new jack funk that didn’t return George to the top of the pops, but did hit the top 5 on Billboard’s R&B chart during the late spring of 1989.
There’s an interview from Spin in which George a) says he’d like to be reincarnated as Matt Dillon’s underwear (!) and b) notes that the collaboration with Riley was an experience he absolutely hated. Regardless of how Mr. O’Dowd felt about “Trip”, though, the man came to work and did his job. His vocal performance is full of sass and vinegar. The Boy even adds in a couple of James Brown “huh”s for emphasis. “Trip” was a cool feather in Riley’s cap, although it often gets forgotten when considering both their catalogs.