Can't Be Heaven (2000)

Danny is falling in love with his best friend Julie, but isn't sure what to do about it. Danny recruits a mentor to help him win Julie's affections, Hubbie Darling, a jazz sax player from the 30's who he happened to meet in the cemetery while visiting his father's grave. Hubbie has his problems though, as he has been dead for 60 years and is refusing to go to heaven until he can be joined by his one true love who is still alive. Hubbie offer's Danny advise and gives him suggestions on how to win Julie over, but what worked in the way of romance in the 30's may not have the same effect in the 90's. Danny finds himself nervous around Julie when she starts hanging out with Archie, the handsome new boy in the class. With Hubbie's advise, he is not only losing Julie's love, but he's getting beat up by the new boy who is also after Julie's affections. But Danny persists, he trusts Hubbie's instincts. Hubbie teaches Danny to play a love song he wrote for his sweetheart, but never had the chance to play it for her. Danny learns the song and plays it beautifully. At a school dance Danny finds a way to show Julie how he feels towards her, he plays the sax which touches Julie who then starts to realize that she feels more for Danny the she thought. But Danny's mettle is tested when he has to defend Julie from a physical attack by Archie. Danny barely wins the fight, but he for the first time asserts himself for Julie. Later, Danny plays the song for Hubbie in the cemetery, Danny's grandmother hears the music and follows it. There in the cemetery, she see's Hubbie. We learn that it is Danny's grandmother Hubbie has been waiting for. Hubbie shows Danny that when two people belong together, nothing can keep them apart, not even death.