Flies on Cupid (2000)

Johnny Hayes, a once upon a time TV star, now down on his luck and in debt with the mob, calls on his close friends Eric and Lisa to bail him out. Johnny faces a whirlwind of problems as he goes about trying to repay his debt, and ultimately finds true love in the arms of his best friend's wife. With a serial killer on the loose, a landlord with mafia blood in his veins, and a gun toting Bohemian girlfriend who is determined to save the day with the help of Johnny's brother. The twisted entanglement finds Johnny, his friends and the rest of the ensemble cast a chronological trip to purgatory!