Hail Caesar

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Hail Caesar VHS front.PNG
From the movie Hail Caesar (1994).

Anthony Michael Hall stars in and also directed this film! He plays Julius Caesar McMurty/MacGruder, a would-be rocker with this band. He works in a pencil eraser factory and makes a bet with his disapproving boss/girlfriend's father that if Caesar can make a ton of money in six months, the boss will let him date his daughter.