Hail Caesar

Hail Caesar (1994) is a comedy directed by Anthony Michael Hall rated 3.4/10.

Caesar is having a hard time dividing his time between his band and his rich girlfriend, Buffer. Buffer's dad doesn't like Ceasar, so he makes Caesar a bet. If Caesar can make a hundred thousand dollars within six months, he can stay with Buffer... but if he fails, their relationship is over forever. How can Ceasar win the bet if he only knows how jam with his band?