

The Underboss
Synopsis
In a world of snitches, con games, and back-room bargains, this eye-popping tapestry of bone-stiffening sex, heart-stopping suspense, and jaw-dropping melodrama has no precedent, no peer, no equal. The Underboss is a magnificent, multi-generational epic that centers around "Mighty Joe," a beautiful professional fighter in the mob's pocket who, after beating up a couple of reporters, gets thrown in the slammer. Mighty Joe's incarceration ignites a labyrinthine series of events that not only exposes the dark underpinnings of the mob's way of life but also threatens the very existence of his mentor, the powerful Underboss, played with razor-sharp perfection by Barresi himself. It's a cinematic mosaic of mystery, mayhem, mesmerizing style, and unparalleled vision that really delivers a knock-out punch! The Underboss shocks and surprises right up to the last unforgettable frame. After all, in Mob-land, the only thing sweeter than sex is revenge!
Top Cast
Explore Star Directory →Winston Love
Angel LeMont
Tommy Cruise
Jailer
Dean Spencer
Inmate
Troy Maxwell
Malone's Boyfriend
Paul Morgan
Jimmy Malone
Dino DiMarco
Shark
Leo Masters
Mickey Leapold
Zach Richards
Bodyguard #1
Dino Phillips
Bodyguard #2
Jason Nikas
Sonny Champa
Alberto Valentino
Mighty Joe
Wayne Cross
Reporter #1
Damien Michaels
Reporter #2
Troy Steele
Russo's Driver
Carmine Rosetti
Fighter
Vincent Barbonni
Referee
Joseph Mastrionni
Corner Man #1
Hunk Hollywood
Corner Man #2
Release History & Theatrical Window
January 1, 2000
Physical Home Media
Key Information & Fast Facts
- Director
- Paul Barresi
- Screenplay & Story
- Paul Barresi
- Original Title
- The Underboss
- Country of Origin
- United States of America
- Spoken Languages
- English
- Runtime
- 1h 44m
- Production Studios
- U.S. Male
Creative Leadership & Key Crew
Paul Barresi
Paul Barresi
John Simms, Christian Wood
Kevin Glover
Alex Katz, Paul Barresi
Department Leadership Roster
Paul Barresi
Director
Paul Barresi
Writer
Kevin Glover
Editor
John Simms
Director of Photography
Paul Barresi
Producer
Christian Wood
Director of Photography
Age Classification & Content Advisories
Official viewer rating standards and content warnings across international classification boards.
NC-17: Adults Only — No one 17 and under admitted.
International Certification Matrix
Adults Only — No one 17 and under admitted.
Production Stills & Gallery
Official cinematic photography and background stills for The Underboss.
Featured In Curated Collections
Editorial lists, community rankings, and cinematic collections featuring The Underboss.
Hermes Watchlist
Combined cinema + adult watchlist (1315 titles).
Similar Titles to The Underboss
Movies sharing stylistic DNA, tone, and thematic storytelling
More Like The Underboss
Recommended titles matching themes, cast, and genres.












Frequently Asked Questions About The Underboss
Quick factual answers about cast, synopsis, director, box office, and release information.
What is The Underboss about?
In a world of snitches, con games, and back-room bargains, this eye-popping tapestry of bone-stiffening sex, heart-stopping suspense, and jaw-dropping melodrama has no precedent, no peer, no equal. The Underboss is a magnificent, multi-generational epic that centers around "Mighty Joe," a beautiful professional fighter in the mob's pocket who, after beating up a couple of reporters, gets thrown in the slammer. Mighty Joe's incarceration ignites a labyrinthine series of events that not only exposes the dark underpinnings of the mob's way of life but also threatens the very existence of his mentor, the powerful Underboss, played with razor-sharp perfection by Barresi himself. It's a cinematic mosaic of mystery, mayhem, mesmerizing style, and unparalleled vision that really delivers a knock-out punch! The Underboss shocks and surprises right up to the last unforgettable frame. After all, in Mob-land, the only thing sweeter than sex is revenge!
Who directed The Underboss?
The Underboss was directed by Paul Barresi.
Who stars in The Underboss?
The principal cast of The Underboss includes Winston Love, Tommy Cruise, Dean Spencer, Troy Maxwell, Paul Morgan.
When was The Underboss released and how long is it?
The Underboss was released in 2000 with a total runtime of 1h 44m.
What is the age rating and content advisory for The Underboss?
The Underboss holds official age classifications: US: NC-17 (Adults Only — No one 17 and under admitted.).


















