James Caan has passed away; a press release was posted on his Twitter account reading: “It is with great sadness that we inform you of the passing of Jimmy on the evening of July 6. The family appreciates the outpouring of love and heartfelt condolences and asks that you continue to respect their privacy during this difficult time.”

Known for his career making role as Vito Corleone’s impulsive but warm-hearted son Sonny Corleone in the 1972 mafia epic The Godfather directed by Francis Ford Coppola, the actor leaves behind 5 children, which includes his son, and fellow actor Scott Caan.

James Caan, or “Jimmy” as he was known by fellow actors, was known for his party lifestyle and dry humor. Caan married four times and most recently worked on the movie Queen Bees. Here are 5 of the best James Caan movies.

5. Brian's Song

Brian's Song was a 1971 movie of the week that aired on ABC where Caan plays Chicago Bears player Brian Piccolo who suffers from terminal cancer after turning pro in 1965. Piccolo establishes an unusual friendship with teammate Gale Sayers (Billy Dee Williams). The film deals with grief and race and is considered one of the best television films ever made.

4. The Glory Guys

A Western made in 1965 where Caan plays Anthony Dugan in a film about two cavalry soldiers who are under the command of a tough general that are fighting Plains Indians and fall in love over the same woman.

3. Bottle Rocket

Wes Anderson’s first movie about a group of wannabe “robbers” is quirky, strange, and loveable. The film stars Owen and Luke Wilson as well as Caan who plays the much more criminally advanced Abe Henry.

2. Misery 

Caan plays an author who is saved from a car wreck by his number one fan, the problem, that fan is completely insane. It is a brutal and edge of your seat look at the obsession fans have with the movies, books, and media that they escape through, even to the detriment of their own lives. Actually, Misery is a great movie to show a classroom today on the dangers of becoming too obsessed with multiverses and media. 

1. The Godfather

The story of a mafia king and his children and how none of the children have the traits of the king. Caan plays Santino "Sonny" Corleone, who is kindhearted and funny as he is brutal and unpredictable. The mafia epic is one of the greatest films ever made, the sequel, where Caan has a cameo, could be one of the five best movies ever made.