Film

Let's Go to Prison

Name: Let's Go to Prison
Genre: Comedy, Crime
Released: 2006
Cast: Dax Shepard, Will Arnett, Chi McBride, David Koechner, Dylan Baker

A low-stakes prison comedy where a career criminal sends his enemy's son to jail, then deliberately gets himself incarcerated to torment him further. It's affably crude, cheerfully stupid, and more interested in hanging out with its hapless characters than delivering plot twists. For people who find 2000s absurdist comedy endearing rather than dated.

TMDb rating

3.0

Should you watch it?

Watch it if you enjoy broad, scrappy buddy comedy where a dim-witted premise is played straight and the chemistry between two mismatched men does the heavy lifting.

Skip it if you want sharp crime with real stakes; the crime side is a loose frame for gags, and the humor leans on crude, repetitive material that may wear thin.

What it asks of you: Under ninety minutes and moving at a brisk clip, it stays loose and silly, rewarding you for laughing at escalating foolishness rather than tracking any complicated plot.

Not sure? Find tonight's pick in a minute.

If you liked this

Old School2003

Same era, same energy: Will Ferrell and friends in ridiculous situations, played straight by everyone involved. The comedy comes from commitment to stupidity rather than cleverness.

But It's very much a product of its time, with jokes that haven't aged gracefully and a shapeless third act that feels like it was written on set.

DodgeBall: A True Underdog Story2004

Vince Vaughn and Ben Stiller in another mid-2000s lark about misfits competing in something ridiculous. Silly without apology, and genuinely funny about the absurdity it's depicting.

But The humour is broad and occasionally mean-spirited. If you hate broad comedy, this won't convince you otherwise.

Anchorman: The Legend of Ron Burgundy2004

Will Ferrell again, this time with Paul Rudd and Christina Applegate. Improvisational energy, no pretensions, a film that knows exactly what it wants to be and commits entirely.

But It's almost entirely carried by its cast's charisma and the director's willingness to let scenes sprawl. If you need plot structure, look elsewhere.

Anchorman: The Legend of Ron Burgundy poster

Not sure tonight? Get a pick in a minute, starting from Let's Go to Prison

The wildcard

Something you would not have found on your own.

Raising Arizona1987

Both use crime as a frame for character comedy rather than vice versa. The plot is an excuse to hang out with criminals who are better at being likeable than being criminal.

The Coen Brothers' heist comedy about two ex-cons stealing a baby. It's structured like a crime caper but played as pure farce. Same DNA as Prison but from actual geniuses who understood the form.

But It's much smarter and faster than Prison, and the performances are layered rather than straightforward. If you prefer comfortable stupidity to sharp wit, you'll feel lost.

The Hangover2009

Todd Phillips directing Zach Galifianakis, Ed Helms, and Bradley Cooper through escalating chaos in Vegas. Tighter than Prison but the same spirit: men in trouble, trying to dig themselves out.

But The third act relies heavily on callbacks rather than new material, and by now the whole thing feels like a template that got endlessly remade.

Role Models2008

Seann William Scott and Paul Rudd are court-ordered to mentor kids; it's stupid in exactly the right way. Character-based comedy that earns its warmth by refusing to be cynical.

But It wraps up with a sincere message about found family that some will find manipulative. The humour also sags occasionally.

Tropic Thunder2008

Ben Stiller, Robert Downey Jr., and Jack Black as actors making a war film in the jungle. Genuinely inventive satire wrapped in broad comedy, and Robert Downey Jr. is fearless.

But The satire can disappear entirely in the second half when it becomes just another action movie. Some of the humour punches down in ways that are hard to defend.

I Love You, Man2009

Paul Rudd and Jason Segel as men becoming friends. Sweet without being maudlin, funny without being mean, and genuinely about something small and real.

But It's very romantic-comedy-shaped, which means predictable beats. Some people hate that structure on principle.

Hot Rod2007

Andy Samberg as a stuntman who wants to jump a canyon to impress his stepdad. Absurdist, weird, committed to its own logic. It's a cult film for good reason.

But It's aggressively silly and won't work if you're not on its wavelength immediately. The humour is very specific and very strange.

Land of the Lost2009

Danny McBride and Will Ferrell in a film nobody asked for, adapted from a TV show nobody remembers. Chaotic, misguided, and actually more fun than it has any right to be.

But It was comprehensively demolished by critics and audiences. It's bad, just in a way that's occasionally entertaining rather than painful.

Weeds2005

Both centre on ordinary people casually entering the criminal world and finding it more comfortable than expected. Prison does it as farce, Weeds does it as tragedy with jokes.

Mary-Louise Parker as a suburban widow who starts dealing marijuana. Eight seasons of sharp, dark comedy about criminality and middle-class desperation. Nancy Botwin is what John could have been in a more cynical world.

But It gets genuinely bleak in the later seasons, and the tonal whiplash is jarring. It's also increasingly messy and loses control of its own logic by season five.

The Animal2001

Both films are committed to the bit even when the bit isn't working. They're uninterested in irony or commentary; they just want to see what a ridiculous premise will do when left alone.

Rob Schneider receives animal organ transplants and gains animal abilities. It's stupid in a way that should be offensive but somehow remains earnest. Pre-dating Prison by five years and hits the same notes of affable, purposeless comedy.

But Rob Schneider is performing here, and his voice will irritate you in seconds if you're not prepared. The joke structure is cartoonish and repetitive, even by low comedy standards.