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The Sopranos wishes it had this much shirtless intrigue.
TMDB
100

The Underboss (2000)

campygrittyover-the-top

Overview

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!

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Content warning
boxingitalian americanmob bossinterracial sexgay pornography
loyalty and betrayalpower and corruptionidentity under pressurefound family

Standout Aspects

Acting

Barresi's self-cast Underboss performance is unhinged commitment.

Direction

Barresi's singular vision—no one else was making THIS movie.

Best for:Solo: When you're in a very specific mood, and that mood is 'campy mob melodrama.'·Rewatch: Guaranteed to reveal new absurdities on every viewing.
Heads up:Sexual Content: Extensive explicit content—this is a gay pornographic film with mob pretensions.·Violence: Prison and mob violence including reporter beatings.
Paul Barresi

Director

Paul Barresi

ReleasedJan 1, 2000
Runtime1h 44m
StatusReleased

Vibe

Pacesteady
Intensityhigh
Tonedark
Feelheavy
U.S. Male

Top Cast

Winston Love

Winston Love

Angel LeMont

Tommy Cruise

Tommy Cruise

Jailer

Dean Spencer

Dean Spencer

Inmate

Troy Maxwell

Troy Maxwell

Malone's Boyfriend

Paul Morgan

Paul Morgan

Jimmy Malone

Dino DiMarco

Dino DiMarco

Shark

Leo Masters

Leo Masters

Mickey Leapold

Zach Richards

Zach Richards

Bodyguard #1

Dino Phillips

Dino Phillips

Bodyguard #2

Jason Nikas

Jason Nikas

Sonny Champa

Damien Michaels

Damien Michaels

Reporter #2

Troy Steele

Troy Steele

Russo's Driver

Ask about The Underboss

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Trivia

Paul Barresi directed, wrote, and starred—triple-threat auteur energy rarely seen outside Ed Wood.

Cultural

A fascinating case study in early-2000s gay adult cinema attempting 'legitimate' genre crossover—The Godfather erotics for a niche audience.

Gallery

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