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Straight boy falls into high-class hustling and catches actual feelings. Chaos ensues.

The Apprentice (1999)

90s indie sleazesex work slice-of-lifegritty romance

Overview

Joe Landon comes home from work to discover that he is no longer welcome. Tossed from the nest, Joe moves on to build a new life in the city. Teaming up with Scott Matthews for play for pay, Joe then meets Chris Rock, who teaches him the ropes on how to succeed in the world of high-class male hustling. The two instantly hit it off and proceed to cross the line between work, sex, and love.

Flag of USUS
gay pornography
economic survivalsexual identityfound familytransactional intimacy

Standout Aspects

Acting

Chris Rock's mentor energy before he was famous-famous

Production

DIY 90s gay indie filmmaking on actual no budget

Best for:Solo: Late-night curiosity spirals you won't admit to anyone·Date Night: If your date's into queer cinema history and zero budget charm
Heads up:Sexual Content: Explicit sex work scenes, softcore-plus territory
B

Director

Barry Knight

ReleasedSep 10, 1999
Runtime1h 46m
StatusReleased

Vibe

Pacesteady
Intensitymedium
Tonemixed
Feelmedium
Delta Productions

Top Cast

Alex Carrington

Alex Carrington

matador

Chris Rock

Chris Rock

Victor, teacher

Joey Stevens

Joey Stevens

clients 2

Marco Antonio

Marco Antonio

client 1

Scott Matthews

Scott Matthews

Connor

Steve O'Donnell

Steve O'Donnell

clients 2

Tony Cummings

Tony Cummings

reporter

Joe Landon

Joe Landon

new escort

Ask about The Apprentice

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Cultural

Part of a wave of 90s gay indie films exploring sex work with surprising empathy rather than moral panic.

Trivia

Chris Rock's early pre-fame role— reportedly took it for rent money and later omitted it from his resume.

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