Hole in the Head, A (1959) - (Movie Clip) Open, All My Tomorrows

Hole In The Head, A - (Original Trailer)

Frank Sinatra is a single father whose swinging lifestyle could cost him custody of his son in Frank Capra's A Hole In The Head (1959).

Hole In The Head A (1959) -- (Movie Clip) Water's Good For You

Brother Mario (Edward G. Robinson), with wife Sophie (Thelma Ritter), is too candid as he introduces widow Eloise (Eleanor Parker) to his brother, cash-strapped Miami hotel owner and single dad Tony (Frank Sinatra), Eddie Hodges the kid, Frank Capra directing, in A Hole In The Head, 1959.

Hole in the Head, A (1959) -- (Movie Clip) A Couple Dollars!

Hotel owner Tony (Frank Sinatra) and older brother Mario (Edward G. Robinson) move from friendly to furious in a discussion about money in director Frank Capra's A Hole in the Head, 1959.

Hole In The Head, A (1959) -- (Movie Clip) Catch Me On The Ninth Wave

Various states of undress for Carolyn Jones as Shirl, divorceè girlfriend of single dad Tony (Frank Sinatra), who’s also her landlord and owner of a struggling Miami Beach hotel, discussing his options, including seeking funds from his grumpy brother, early in Frank Capra’s A Hole In The Head, 1959.

Hole in the Head, A (1959) -- (Movie Clip) High Hopes

Dad Tony (Frank Sinatra) and son Ally (Eddie Hodges) with Jimmy Van Heusen and Sammy Cahn's Academy Award-winning novelty hit song, a version of which became a theme for the Sinatra-backed Kennedy presidential campaign, in director Frank Capra's comeback, A Hole in the Head, 1959.