The Fresh Prince Of Bel-Air: Bourgie Sings The Blues
Series 6 episode 4 from 1995.
Carlton is on a real downer as nothing is going right for him.
He can’t even get a job as a volunteer.
Will tries his best to pick him up but he ends up in a bar where everyone else is down as well.
The resident blues singer is BB King.
In the end, Carlton comes round and it works out well, when his Princeton application is accepted.
Movie pages here.