Boss of Bosses is a 2001 American made-for-TV movie about the life of former Gambino crime family boss Paul Castellano directed by Dwight H. Little. It stars Chazz Palminteri as Paul Castellano, Patricia Mauceri as his wife Nina, Mark Margolis as Joseph Armone, and Angela Alvarado as his mistress Gloria Olarte.
The film focuses on Paul growing up, becoming disenchanted with his working class lifestyle, spending time and being influenced by his cousin Carlo Gambino, his friendship with Joseph Armone and Tommy Bilotti, and also on his growing relationship with his maid Gloria. The film serves as a companion piece to Gotti. As "Boss of Bosses" climaxes with Paul Castellano's murder, while Gotti focuses on the events before, during and after the murder.
The film documents his rocky relationship with his soldiers, along with friend Neil Dellacroce, and climaxes when he attends the famous "meeting" at Sparks Steak House, where he and his bodyguard/underboss Tommy Bilotti are murdered as they exit their vehicle in an ambush arranged by John Gotti.
- Chazz Palminteri as Paul Castellano
- Angela Alvarado as Gloria Olarte
- Firmine Richard as Solange / Florence Gentil
- Jay O. Sanders as Joseph O'Brien
- Clancy Brown as Andris Kurins
- Richard Poronjy as Tommy Bilotti
- Mark Margolis as Joseph "Piney" Armone
- Dayton Callie as Neil Dellacroce
- Patricia Mauceri as Nina Castellano
- Al Ruscio as Carlo Gambino
- Sonny Marinelli as John Gotti
- Philip Williams as Nino Gaggi
- Steven Bauer as Vito Genovese
- Yani Gellman as Young Paul Castellano
- William DeMeo as Young Carlo Gambino
- Carlos Díaz as Philip Castellano
- Gerry Mendicino as Father Vicente
- Reagan Pasternak as NYU Student