Film

My Old School

Name: My Old School
Genre: Documentary, Animation
Released: 2022
Cast: Alan Cumming, Clare Grogan, Lulu, Dawn Steele, Joseph McFadden

Coming-of-age

A Scottish documentary-animation hybrid about a teenager who conned his way into a prestigious Glasgow school, narrated by Alan Cumming. It's playful and inventionally told—mixing interviews with charming hand-drawn sequences—making a true story of audacious deception feel like the caper it actually was. For anyone who loves a well-executed con, clever storytelling, or Scottish character.

TMDb rating

3.5

Should you watch it?

Watch it if you enjoy true stories that get reshaped by memory and performance, and you like a documentary that trusts animation to show what people remember rather than what was filmed.

Skip it if you want a straight-faced documentary with archive footage and hard facts, since this prefers mood and anecdote to the record and wanders over a full hundred minutes.

What it asks of you: Settle in for an hour and forty minutes with a loose, rambling rhythm that rewards patience more than attention, and a tone that swings from mischievous to melancholy.

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

If you liked this

The Wolf of Wall Street2013

A charismatic con artist charms his way upward through sheer audacity and charisma. Like Brandon Lee, the protagonist's greatest talent is convincing people he belongs in rooms he doesn't. Both celebrate the mind of the scammer.

But Three hours long, often bleak, and the lifestyle it depicts is genuinely toxic and harmful. The film doesn't hold back on depicting that cost.

Catch Me If You Can2002

The quintessential con-artist film: a young man impersonates an airline pilot, a doctor, a lawyer. It's charming and clever without being brutal. Spielberg and DiCaprio make the deception feel like intellectual sport.

But Occasionally slips into a tone that's too admiring of crime. Some find the romance subplot distracting from the con itself.

American Hustle2013

A stylish ensemble con film set in the 1970s where the con is the point, not the crime. Like My Old School, it treats deception as a kind of art form and finds humor in the audacity of it all.

But The plot is deliberately convoluted and some scenes feel self-indulgently long. If you want clarity and forward momentum, this meanders.

Not sure tonight? Get a pick in a minute, starting from My Old School

The wildcard

Something you would not have found on your own.

TÁR2022

Both explore how charisma and institutional access allow someone to maintain a false identity. Both are ultimately about the psychology of performance, not the logistics of the deception.

A conductor uses institutional power and charisma to maintain an elaborate deception about who she is and what she's done. The con here is psychological and institutional rather than criminal, and it operates on a subtler register—how power makes lying invisible.

But Three and a half hours of slow-burn psychological unraveling. Cate Blanchett speaks often in jargon. If you need plot movement over character immersion, this will feel glacial and pretentious.

The Grifters1990

A tense, character-driven film about people for whom lying is survival. Anjelica Huston is extraordinary. It captures what happens when you're so committed to a con that you forget who you actually are.

But Considerably darker than My Old School. There's no charm here, only desperation and moral erosion. It's a cautionary tale, not a romp.

GoodFellas1990

Henry Hill's rise through sheer charisma and the ability to operate in spaces he wasn't born to occupy. Scorsese's masterpiece about charm, ambition, and the world rewarding the people who take what they want.

But Extremely violent and structured around crime and corruption as intoxicating rather than corrupt. If that moral framing bothers you, it's difficult to move past.

The Talented Mr. Ripley1999

A con artist assumes identities in sun-soaked Italy, winning people over through pure performance. It's elegant and deeply unsettling—the con here is psychological rather than financial, and all the more fascinating for it.

But Deliberately paced and ambiguous. If you need clear moral resolution or fast-moving narrative, the film's meditative stance will frustrate you.

The Sting1973

Newman and Redford orchestrate an elaborate con against a mob boss. It's pure fun—the con is the plot, the execution is the spectacle, and the film celebrates the sheer cleverness of getting away with it.

But Quite dated in style and structure. Some younger viewers find the pacing slow and the twists predictable by modern standards.

Matchstick Men2003

Nicolas Cage as a con artist with OCD. It's quirky, character-focused, and genuinely funny about the psychology of someone who lives by manipulation. The con reveals are satisfying.

But The twist ending divides audiences sharply. Some find it revelatory; others feel it invalidates what came before. It's a gamble.

Heist2021

A limited series about real con artists and their most audacious schemes. Stylish, fast-paced, and genuinely thrilling. Each episode is a masterclass in how deception actually works in practice.

But Documentary-style realism means some schemes fall flat in execution, unlike the Hollywood versions. If you want narrative satisfaction, real life often disappoints.

Summer Heights High2007

Both use the high school setting to explore performance and the psychology of adoption of false identity. Both find the humor in the sheer audacity of someone succeeding by simple reinvention.

An Australian mockumentary where Chris Lilley plays three students at a high school, each with different levels of audacious fakeness. It's a comedy, but it nails the same nerve My Old School does—the surreal experience of watching someone pull off the impossible.

But Comedy-centric rather than documentary. Lilley's performance style is broad and occasionally grating. If you want the story played straight, the comedic inflation might undercut your investment.

Three Billboards Outside Ebbing, Missouri2017

Both explore how someone can control a narrative and bend institutions to their will through sheer force of character and performance. Both celebrate that audacity while remaining complex about its costs.

A woman performs anger and certainty as a tool to make the world bend to her will. Like Brandon Lee, she understands that confidence and narrative control can move mountains. It's about performance as power.

But Dark subject matter involving violence and grief. The tonal shifts between comedy and genuine tragedy are abrupt. Some viewers find the moral ambiguity of the protagonist frustrating.