Frank Sinatra sings his way through the screwball musical comedy Higher and Higher. When the members of Cyril Drake's (Leon Errol) household staff discover that he is about to declare bankruptcy--and put them all out of work--the concoct a plot to save his fortune: They plan to pass pretty scullery maid Millie (Michèle Morgan) as an eligible heiress. But the man they lure, Sir Victor Fitzroy Victor (Victor Borge) is as poor as she is. Frank Sinatra sings "I Couldn't Sleep a Wink Last Night" and "This is a Lovely Way to Spend an Evening."