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Charlie Sheen having a pre-marriage crisis with his boys? What could go wrong.
TMDB
58
IMDb
51
Rotten Tomatoes
10
Audience Score
10

Five Aces (1999)

90s bro nostalgiaquarter-life crisischeap beer energy

Overview

ComedyDrama

Chris Martin has a problem: his impending marriage. Like any other man about to enter into the holy vows of matrimony, Chris has begun to second guess himself. Is married life what he really wants? While his bride-to-be takes care of the wedding plans, Chris returns to the neighborhood of his youth to consider his married future and to spend one last week of bachelorhood with his four high school buddies: Ray, Ash, Todd and Sean. Together, the reunited "Five Aces" enjoy a funny bittersweet week reminiscing about a time when they had all the answers... only nothing turned out the way they planned. As the week's events unfold, the Five Aces begin to realize exactly what life and friends mean to each other.

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Content warning
friendship vs. commitmentfear of growing upmasculine vulnerabilityregret and reconciliation

Standout Aspects

Acting

Charlie Sheen actually trying in a dramatic role? Surprisingly watchable.

Writing

Dialogue that feels like actual dudes talking, not Hollywood's idea of dudes.

Best for:Solo: When you miss your old crew and need a good cry-laugh.·Background: Perfect for folding laundry while half-watching 90s guys be emotional.
D

Director

David Michael O'Neill

ReleasedMay 28, 1999
Runtime1h 40m
StatusReleased

Vibe

Pacesteady
Intensitymedium
Tonemixed
Feelmedium
Budget$3M

Top Cast

Tia Carrere

Tia Carrere

Karen Haggerty

Charlie Sheen

Charlie Sheen

Chris Martin

Christopher McDonald

Christopher McDonald

Ash Gray

Jeff Cesario

Jeff Cesario

Todd Lackey

David Sherrill

David Sherrill

Ray Vanowen

Michael McGrady

Michael McGrady

Sean Haggerty

Aimée Leigh

Aimée Leigh

Shauna

Shawn Weatherly

Shawn Weatherly

Jackie

Barbara Moore

Barbara Moore

Rosanne Barton

Geoffrey Lewis

Geoffrey Lewis

Sloan

Matt Clark

Matt Clark

Phillip

Virginia Hamilton

Virginia Hamilton

Kelly

Patricia Skeriotis

Patricia Skeriotis

Sofia Panagoulis

Ask about Five Aces

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Trivia

This was David Michael O'Neill's only feature directing credit; he spent most of his career as a TV writer-producer on shows like Nash Bridges.

Cultural

Released the same year as American Pie, this is the forgotten, sadder cousin of 90s 'one last ride with the boys' cinema—less pie-fucking, more actual fear of adulthood.

YouTube

Five Aces

Five Aces

Gallery

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