"Two Shots of Happy, One Shot of Sad" is a song Bono and The Edge of U2 wrote during the group's Zooropa ('92-'93) tour. It was written with Frank Sinatra in mind, and it was Bono's attempt to compose in the style of Sammy Cahn/Jimmy Van Heusen, Cole Porter, Johnny Mercer, etc., etc. Bono had hoped the aging crooner would record it, and he made several attempts to get Sinatra to at least hear it. 
Sinatra never did record again after the Duets albums (although daughter Nancy recorded a version of "Two Shots of Happy, One Shot of Sad" for her 2004 Nancy Sinatra album), but it was during the filming of the video for the Bono/Sintra duet of "I've Got You Under My Skin" that Bono's final opportunity to "sell" the song arrived. The elderly Sinatra reportedly became extremely disoriented, and consequently, agitated, during the making of the video and made an abrupt exit. According to Bill Flanagan's U2: At the End of the World:
"Bono gets a call from Barbara (Sinatra's wife) apologizing for Frank's hasty exit and inviting him over to the house that evening. Bono says sure, and he arrives to a night of whiskey drinking and storytelling with Sinatra and about six of his pals (oh, to have been a fly on the wall!!). Frank seems fine now, and completely in his element. Eventually Bono proposes a toast, stands up, raises his glass--and sings "Two Shots of Happy" for Frank and his cronies. Sinatra smiles as he listens. Bono decides that's going to have to be good enough (p. 399)."
Here are Bono and The Edge performing it in 1995, via satellite, on the televised, Sinatra, 80th birthday celebration (Sinatra: 80 Years My Way):
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