Life with Louie (1994)

S2E1 Caddy on a Hot Tin Roof

Louie lands a summer gig as a caddy to make some extra money and quickly turns into Jojo Stomopolous's lucky charm and personal assistant. Jojo is the local snob at Pinenut Country Club, and Louie finds himself navigating the ups and downs of their quirky relationship while trying to keep up with the demands of his new role.