Film

The Underdog's Tale

Name: The Underdog's Tale
Genre: Comedy, Romance
Released: 2007
Cast: Brad McMurray, Elise Greig, Leonard Goldberg, Evert McQueen, Dawn Albinger

A scrappy 2007 comedy about a self-aware disaster of a man chasing love across 73 minutes of romantic chaos. It's the kind of film that knows exactly how messy its protagonist is and leans hard into the laugh-at-yourself energy. Made for people who find charm in characters that nobody else would bet on.

Should you watch it?

Watch it if you like scrappy, self-deprecating romantic comedies where the hero is a mess and the funny comes from his bad decisions in pursuit of love.

Skip it if you want a tidy, sharp romance, since this one is loose and sprawling, and its jokes about drinking and fringe characters may grate if that's not your sense of humour.

What it asks of you: Seventy-three minutes, so it moves quickly; you'll need to go along with its rough edges and a sense of humour that runs on mess and bad judgement.

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

If you liked this

I Love You, Man2009

A genuinely funny romantic comedy about a groom-to-be who needs to find a best man, starring Paul Rudd and Jason Segel. Smart, warm, and never settles for easy jokes—it actually likes its characters.

But If you want pure romance, the emotional weight stays light. The humour is front-loaded and some gags land softer than others.

Forgetting Sarah Marshall2008

Jason Segel again, but this time as a heartbroken composer trying to move on at a Hawaiian resort. Hilarious, kind-hearted, and genuinely invested in its people rather than just the setups.

But The raunchier moments might feel dated if you're looking for something timeless. Some secondary characters exist just to be annoying.

Knocked Up2007

Judd Apatow's sprawling comedy about an unexpected pregnancy and the slacker guy at its centre. Messy, funny, weirdly touching about commitment and growing up without being preachy.

But It's 129 minutes and not every subplot earns its space. Some relationship dynamics haven't aged perfectly well.

Not sure tonight? Get a pick in a minute, starting from The Underdog's Tale

The wildcard

Something you would not have found on your own.

Better Off Dead...1985

Both are underdog-centred romantic comedies that love their messy protagonists and find humour in their specific brand of disaster without punishing them for it.

A deadpan indie comedy about a teenager trying to win back his ex-girlfriend and simultaneously not killing himself. Visually inventive, genuinely weird, and funny in ways that feel handmade rather than factory-assembled.

But The tone is strange—comedy and darkness sit uncomfortably close. If you need clarity on whether you're meant to laugh, this will frustrate you.

DodgeBall: A True Underdog Story2004

Vince Vaughn and his underdog gym team versus a corporate fitness empire. Pure stupid fun with an actual heart underneath, and it commits fully to its own dumb premise.

But If you need a plot that makes sense, this isn't it. The humour is deliberately broad and relies on you being on its wavelength.

The 40 Year-Old Virgin2005

Steve Carell as a genuinely likeable mess trying to lose his virginity with friends who actually care about him. Tender underneath the crude humour, and Carell makes you root for his disaster of a man.

But Runs nearly two hours and the romance subplot takes a while to arrive. Some of the sexual humour is aggressively 2005.

Tropic Thunder2008

A war film parody about terrible actors making a terrible Vietnam War film. Stacked cast, committed to the bit, genuinely clever about showbiz delusion and method acting taken to ridiculous extremes.

But The satire can feel scattershot. If you're not familiar with the films it's parodying, some of the best jokes won't land.

Role Models2008

Seann William Scott and Paul Rudd as court-ordered mentors to troubled kids. Chaotic, surprisingly earnest about mentorship and friendship, and the whole thing has zero pretence.

But It's built on a thin premise and happy to stay there. Some jokes feel very specifically 2008 and haven't travelled well.

Old School2003

Will Ferrell as a middle-aged divorced man returning to college. Defiantly stupid comedy that owns what it is, and Ferrell's commitment to the chaos is infectious.

But It's purely comedic—no real emotional arc. If you need your laughs tethered to character growth, you'll feel like something's missing.

National Lampoon's Van Wilder2002

Ryan Reynolds as the perpetual college student who won't grow up. Likeable in its slacker sensibility, and genuinely funny about the absurdity of refusing to leave university.

But The romance feels bolted on and takes forever to matter. Dated faster than it had any right to, and some secondary characters are purely filler.

Peep Show2003

Like Eric chasing love while being fundamentally unwell, Peep Show is built on characters who want connection but actively wreck it—and the comedy comes from understanding exactly why.

British comedy series told entirely in first-person POV, alternating between two flatmates' internal monologues. Painfully funny about neurosis, self-sabotage, and loving people you actively disappoint—it's a masterclass in character comedy.

But Nine seasons is a commitment. The cringe builds and rarely resolves, and if you need your protagonists to learn and improve, you'll leave disappointed.

After Hours1985

Both centre on a man's escalating humiliation in pursuit of connection, but where Underdog's Tale is scrappy and earthbound, After Hours transforms that same desperation into stylized nightmare—same emotional engine, completely different register.

Martin Scorsese directing a man's nightmarish odyssey through downtown Manhattan after a date goes wrong. Surreal, stylish, absurdist in the best way—a fever dream comedy that feels nothing like typical romantic chaos.

But It's genuinely unsettling underneath the humour. The tone is so distinctive that if it doesn't click immediately, nothing will save it.