These Sales Movies Will Make You Quit… Or Double Down

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After a long week of dealing with hangups, sales objections, and the occasional psycho boss, there’s nothing quite like kicking back and watching some quality sales movies or TV series. The ones that really nail what it’s like to be in this crazy profession. 

So grab a cold one, put your feet up, and get ready to alternate between nodding along vigorously and yelling “SAME!” at the screen. Because let’s face it, sometimes the only way to stay sane in sales is to revel in the completely insane scenarios Hollywood throws at us sales professionals. Here’s the list of all time best sales movies and my personal favorites:

The Best Sales Comedy Movies

Sometimes, the only way to cope with the soul-crushing craziness of being a sales rep is to laugh through the pain. Whether you’re peddling B2B SaaS, overpriced knives, or some too-good-to-be-true pharmaceutical miracle, these comedy sales movies let you indulge in the absurdity of it all.

From sending up corporate doublespeak to embracing the ridiculous lengths sales professionals go for a commission, these funny sales movies cut through the BS with gut-busting honesty. Who knows, you might even laugh so hard you forget that crippling sense of emptiness for a couple hours!

Thank You for Smoking (2005)

Thank You for Smoking (2005) - The Best Sales Comedy Movie

Sales Hustle Realism

The BS rationalizations? Sadly accurate.

Rags to Riches Inspo

Getting rich by ruining lives isn't super uplifting.

Sales Lessons

If you can argue, you can sell anything, even cancer.

“Thank You for Smoking” is a satire so sharp it’ll slice right through your sales pipeline and sever those prospective sales leads faster than you can type “Hi Jake, I hope this email finds you well.” Aaron Eckhart plays Nick Naylor, a sales rep for Big Tobacco who can sell sand in the desert.

This sales movie pulls no punches in exposing the corrupt sales practices of the tobacco marketing industry. Naylor is a successful salesman who’d sell his own mother for a nickel – if she wasn’t already six feet under from puffing his products. His only loyalty is to the almighty dollar and his mantra is “buy, buy, buy” no matter how many unsuspecting buyers get led to an early grave.

“Thank You for Smoking” takes unforgettable satirical aim at the sales game and the many sales reps willing to compromise ethics for a sale. It’s a brutally funny must-watch for anyone looking for dark comedic movies about sales success.

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The Goods: Live Hard, Sell Hard (2009)

The Goods - Live Hard, Sell Hard (2009) - The Best Sales Comedy Movie

Sales Hustle Realism

A bit exaggerated, but we've all had those desperate days.

Rags to Riches Inspo

If slinging lemons is your dream, go for it!

Sales Lessons

Might learn some tactics. Also how to get sued.

Sales reps know the drill – grinding through another month, hustling to hit your numbers and make sales quota. When the grind gets you down, sometimes you need a pick-me-up in the form of a funny sales movie that captures the seedy underbelly of the sales game. “The Goods: Live Hard, Sell Hard” is a great choice.

This movie is all about a hired sales team brought in to save a struggling used car lot. Jeremy Piven plays the alpha dog sales rep Don Ready, a maniacal closer who lives for the thrill of the sales process. He’s joined by a motley crew of salesmen who are just as morally bankrupt as Don.

What ensues is a glorious circus of unethical sales practices, screwing over unsuspecting buyers, and general degeneracy. It’s like the writers said “What’s the most depraved way sales reps could act?” and then rolled with it. This movie gives zero Fs about political correctness. But that’s what makes it brilliant satire and such a guilty pleasure for sales reps! Plus it’s got a million laugh-out-loud moments that’ll have you crying tears of joy.

The Joneses (2009)

The Joneses (2009) - The Best Sales Comedy Movie

Sales Hustle Realism

An exaggerated yet insightful take on lifestyle selling.

Rags to Riches Inspo

Living a total lie isn't super uplifting or inspirational.

Sales Lessons

Sell a lifestyle, not just a product.

Sales movies don’t get much more devious than The Joneses. This sales movie pulls back the curtain on those annoyingly perfect families who make you feel like a loser for not having the latest toys and threads. Turns out the Joneses aren’t really relatives – they’re an undercover sales team hired by corporations to push product on unsuspecting buyers.

Talk about a high pressure sales job! These “sales reps” have to live, breathe and practically procreate the materialistic dream to convince their neighbors to consume like it’s Black Friday every day. It’s enough to make any sales rep feel dirtier than a used car salesman’s mouth.

The movie is a delicious satire that exposes the soulless core of sales strategies designed to turn people into relentless spenders on an infinite loop.

Love & Other Drugs (2010)

Love & Other Drugs (2010) - The Best Sales Comedy Movie

Sales Hustle Realism

Perfectly captures the unique "charm" of pharma sales.

Rags to Riches Inspo

Getting laid and rich is okay inspiration, I guess?

Sales Lessons

Plenty of prime lessons in exploiting people's insecurities.

Oh boy, do I have a “sales movie” for you – “Love & Other Drugs”! This movie stars Jake Gyllenhaal as Jamie Randall, a pharmaceutical sales rep pushing Viagra, Zoloft, and other magic pills with the kind of sleazy charm you’d expect from a sales rep from a Chicago real estate office.

The guy’s worming his way into doctors’ offices, schmoozing physicians, and out-hustling that Prozac-peddling douchebag Trey to make it to the big leagues in Chicago. Corrupt sales practices and sales strategies? Who cares, he’s just trying to make that money like every other sales rep out there!

Of course, Jamie’s world gets flipped when he meets Maggie (Anne Hathaway) and they get tangled up in a steamy mess of bedsheets. I won’t spoil what happens next. Go watch it!

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The Internship (2013)

The Internship (2013) - The Best Sales Comedy Movie

Sales Hustle Realism

The tech world may be different, but the hustle is familiar.

Rags to Riches Inspo

Rags to Googlers – modern day American dream?

Sales Lessons

Some decent lessons in networking and adaptability.

Look, being a sales rep ain’t easy, especially in this digital age. Just ask Billy and Nick, those two washed-up sales reps played by Vince Vaughn and Owen Wilson in “The Internship”. These two poor schmucks lost their sales gig selling wristwatches when their company went belly-up. Nobody needs a damn watch anymore, not when we all got phones telling us the time.

So what do a couple of middle-aged sales reps do when the rug gets pulled out from under them? They desperately start searching for “jobs for people with no skills” and somehow land internships at… Google. Yeah, Google, that big tech company that makes the world a better place… according to the movie.

Google

Somehow these two losers get accepted into Google’s internship program to compete for real jobs. They’re the oldest Googlers there, getting mercilessly mocked by the college kids. Can’t blame the young’uns – Billy and Nick are so behind the times, they make Willy Loman look cutting-edge.

“The Internship” is formulaic but has a lot of heart. It’ll make you laugh and maybe even appreciate those sales reps who persevere against all odds. Just don’t expect too many groundbreaking sales game – this sales movie is all about poking fun at the sales hustle.

Tommy Boy (1995)

Tommy Boy (1995)- The Best Sales Comedy Movie

Sales Hustle Realism

Clumsy sales tactics, but with heart.

Rags to Riches Inspo

From doofus to hero.

Sales Lessons

Persistence and personality can sell anything.

In sales, you gotta have the right pitch, know your target audience, and be ready for some serious high pressure sales tactics… every now and then. Well, “Tommy Boy” is a cinematic “master piece” that’ll make you question if the sales reps behind it were huffing brake fluid. It’s a fun sales movie, don’t get me wrong.

This movie follows Tommy Callahan (Chris Farley), an automotive sales rep who couldn’t sell a life raft to a drowning man. When his dad’s brokerage firm hits some potholes, Tommy hits the road with his frenemy Richard (David Spade) to chase down some prospective sales leads. What ensues is a sales strategy so misguided, you’d think they were trying to sell maple syrup to Canadians.

From pathetic sales pitches to cars literally disintegrating around them, “Tommy Boy” is a sales documentary on how NOT to run a sales process. It’s like watching sales reps set themselves on fire as a sales tactic. Yet there’s a twisted charm to watching these two clowns fail upwards.

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The Best Sales Movies About Underdogs

Let’s face it, us sales reps are the underdogs of the corporate world. We’re the schmucks on the front lines taking all the abuse, chasing sales quotas, and getting zero respect. But these underdog sales movies celebrate the hard-luck sales reps who may be down, but are never truly out.

These heroes may not move major units or make the big bucks, but they’ve got more heart than an entire team of Wolf of Wall Street rejects.

Cedar Rapids (2011)

Cedar Rapids (2011)- The Best Sales Comedy Movie

Sales Hustle Realism

Insurance sales with Midwest charm.

Rags to Riches Inspo

More like rags to slightly better rags.

Sales Lessons

Integrity counts, even at a convention.

Cedar Rapids is a sales movie that takes a brutally honest look at the sales reps world through the eyes of Tim Lippe, played by Ed Helms. This poor schmuck gets thrown into the shark-infested waters of an insurance sales convention, thinking he’s following in the footsteps of his idol, the “Christian values” poster boy Roger Lemke.

Boy, is he in for a rude awakening when he finds out Lemke was a sleazebag who bribed his way to sales success. Tim’s journey from wide-eyed newbie to jaded sales rep is both hilarious and heartbreaking.

While not exactly a feel-good sales movie, it’s a dark comic gem that any sales rep who’s been around the block will relate to.

Suckers (2001)

Suckers (2001) - The Best Sales Comedy Movie

Sales Hustle Realism

Sleazy car lot tactics – painfully real.

Rags to Riches Inspo

More like sleaze to slightly less sleaze.

Sales Lessons

High-pressure sales tactics 101 – effective but dirty.

Suckers (2001) is a little-known sales movie that never even got a proper U.S. release. It follows Bobby DeLuca (Louis Mandylor), a sales rep in debt who takes a high pressure sales job at a car dealership brokerage firm run by the unscrupulous Reggie (Daniel Benzali).

To become the top sales rep and earn the bonus to pay off his debts, Bobby has to abandon being a “nice guy” and embrace dirty sales practices like lying… no surprise there. Meanwhile, there’s a drug trafficking subplot involving Reggie that feels a bit disconnected from the main sales career storyline. But that’s ok.

The movie wants to be a dark comedy about dirty sales processes, but oftentimes it misses the mark. The sales training scenes where Reggie coaches his sales team on manipulative tactics do ring true for anyone in sales.

While Louis Mandylor gives a solid performance showing Bobby’s transformation from quiet to cutthroat sales rep, the movie never quite figures out what it wants to be. The car dealership setting is interesting, but the misguided criminal subplot derails the movie in my opinion. Still, this movie is worth a watch.

Cadillac Man (1990)

Cadillac Man (1990) - The Best Sales Comedy Movie

Sales Hustle Realism

If you think used car salesmen have it easy, think again.

Rags to Riches Inspo

Climbing from the gutter to the curb.

Sales Lessons

Charm can sell cars, desperation closes the deal.

Cadillac Man stars Robin Williams as Joey O’Brien, a broke womanizer of a car sales rep who really needs to sell a bunch of cars at the big weekend sale to keep his job at the car dealership. The first half sets him up as a sleazy salesman hitting on the hot receptionist Donna and fighting with his ex-wife and mistress.

Just when you think it’s going to be a cheezy comedy about salesmen telling lies and pulling dirty tricks, Donna’s unstable husband (Tim Robbins) crashes through the dealership window on a motorcycle waving a machine gun, taking everyone hostage!

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Easily video-narrate sales presentations or proposals when needed (otherwise video is optional). Redo slide if you made a mistake. Use built-in teleprompter to record longer videos.

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The Best Sales Drama Movies

These iconic sales movies pull back the curtain on the seedy underbelly of chasing commission checks at all costs. Whether you find these hard-hitting sales films inspiring, depressing, or just totally outrageous, one thing’s for sure – they’ll make you grateful your job merely involves robocalling during dinner hours.

The Company Men (2010)

The Company Men (2010) - The Best Sales Drama Movie

Sales Hustle Realism

The job market is a brutal sales floor.

Rags to Riches Inspo