A Hole in the Head
(1959)

Tony (Frank Sinatra) keeps coming up with get rich schemes to support him and his son and they don't work.

His latest scheme has him trying to get one of his friends to finance one of his schemes, an amusement park.

To impress his old friend he sells his Cadillac for money to impress his friend at the dog races and loses all his money.

Tony Manetta does not get the money and does not stay with Shirl (Carolyn Jones) he ends up with the divorcee Eloise Rogers (Eleanor Parker) that his brother and sister in law set him up with.

 Thanks Fern!