"High Hopes" was a little more recent, 1959, with music by James Van Heusen and words by Sammy Cahn. It was introduced in the non-musical motion picture A Hole in the Head by Frank Sinatra and Eddie Hodges. The song received the Academy Award. It was written as a last-minute decision, because of the sudden need for a song in an emotional scene in an otherwise non-musical motion picture. The song was used to promote John F. Kennedy's presidential campaign in 1960.

"Swinging on a Star" was published in 1944, with words by Johnny Burke and music by James Van Heusen (so there is a connection). It was introduced by Bing Crosby and a boys' chorus in the 1944 motion picture Going My Way. Both the song and the movie received the Academy Award.
Johnny Burke and Van Heusen were dining at Bing Crosby's when one of Bing's sons misbehaved. Bing scolded him for acting like a mule. Burke, who had been worrying about a song for one of the scenes in Going My Way, found in this incident a suitable song subject: about somebody, stubborn as a mule, refusing to better himself. The next day, Burke and Van Heusen wrote their song.

Source: American Popular Songs: from the Revolutionary War to the Present, by David Ewen, 1966.

-Joe Offer-