These Sales Movies Will Make You Quit… Or Double Down

Written by DeckLinks Team

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” 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.

The Goods: Live Hard, Sell Hard (2009)

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)

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)

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!

The Internship (2013)

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.

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)

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.

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 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 (1999)

Suckers (1999) 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 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!

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)

I gotta say, “The Company Men” is a pretty spot-on depiction of the harsh realities facing sales reps in today’s economy. Ben Affleck stars as Bobby, a hotshot VP of Sales at GTX – a transportation conglomerate – where the mantra “We need to get the stock price up” leads to mass layoffs and a whole lot of misery for the sales team.

Bobby goes through the five stages of grief after losing his sales job, trying to maintain his trophy home, trophy Porsche, and trophy wife while desperately searching for a new sales gig in a brutally competitive job market. It’s a relatable tale for any sales rep or general manager who’s ever found themselves suddenly out of work and struggling to keep up appearances.

The film hits all the classic sales movie tropes – the corrupt sales practices, the ruthless CEO, the principled division head fighting for his sales team – but it does so with a bit of dark humor.

The Wolf of Wall Street (2013)

If you want to see the slimy, depraved side of the sales game, look no further than The Wolf of Wall Street. This true story shows the rise and historic face-plant of Jordan Belfort, a successful salesman who conned his way to millions through some of the most unethical sales practices ever put to film.

Leonardo DiCaprio plays Belfort as this wired, profanity-spewing boiler room stock broker who makes Gordon Gekko look like a Boy Scout. From riling up his sales team of wannabe wolves with a pep talk that would make a pimp blush, to the office parties that would make Caligula say “damn, too much” – this movie pulls zero punches. It’s one of the top sales movies.

It’s basically a glimpse into the blackest souls of many sales professionals on Wall Street who wouldn’t think twice about selling their own grandmother a busted oven if it meant hitting their sales quotas. The guy’s hustle and sales strategies for parting naive people from their money is so dirty, it’ll make you question your own sales career.

The Founder (2016)

“The Founder” tells the true story of how Ray Kroc, a struggling sales rep, turned McDonald’s into a global fast-food empire. But don’t expect any feel-good lessons about hard work and perseverance – this is a tale of ruthless ambition and dirty sales practices.

Michael Keaton plays Kroc, a fast-talking, hard-drinking sales rep who stumbles upon the McDonald brothers’ revolutionary restaurant concept and decides to franchise the hell out of it. Watching Kroc use every dirty trick in the book to steal the business from under the brothers’ noses is like watching a master class in unethical sales strategies.

But here’s the thing, as much as you might grudgingly admire Kroc’s sales skills, the guy is the kind of person who’d sell his own grandmother if it meant closing a deal. Still, if you’re in sales, you might pick up a few sales tricks from watching Kroc work his magic. Just don’t blame me if you end up feeling like you need a long, hot shower afterwards to wash away the stench of moral decay. And if you’re looking for an uplifting sales movie that won’t make you question your faith in humanity, maybe stick to something like “Jerry Maguire” instead. At least in that one, the character Tom Cruise is playing has a conscience.

Glengarry Glen Ross (1992)

Glengarry Glen Ross” is one of the best sales movies that captures the cutthroat world of real estate salesmen. Based on David Mamet’s play, this film is a masterclass in high pressure sales, showcasing the desperate measures sales reps will take to close a deal and keep their jobs.

The movie revolves around a group of real estate salesmen, each struggling to make sales and avoid being fired. Alec Baldwin’s character, Blake, delivers a scathing motivational speech, setting the stage for a ruthless sales contest where first prize is a Cadillac, second prize is a set of steak knives, and third prize is unemployment.

The film’s cast, including Al Pacino, Ed Harris, and Alan Arkin, delivers sharp, profanity-laced dialogue, exposing the underbelly of the sales world. “Glengarry Glen Ross” is a must-watch for anyone in sales, offering a dark comedic yet poignant look at the lengths sales professionals will go to survive in a competitive world.

Boiler Room (2000)

“Boiler Room” is a sales movie that hits all the right notes for sales reps. Writer-director Ben Younger may try to pull a fast one on us by pretending it’s some deep dive into the seedy world of corrupt sales practices, but we all know the real draw is watching a bunch of young kids working the sales game. 

“Boiler Room” centers around Seth Davis (Giovanni Ribisi), a college dropout running an illegal casino who gets lured into a sketchy brokerage firm by the flashy cars and fat commissions. Ribisi totally nails the part of the underdog salesman just trying to make it in this cold, competitive world. As Seth gets indoctrinated into the world of high pressure sales, learning all the slick sales strategies from Wall Street vets like Greg Weinstein (Nicky Katt), you can’t help but root for the kid.

The Big Kahuna (1999)

I can tell you that “The Big Kahuna” is one of those sales movies that hits close to home. It’s like a twisted version of a sales professional’s wet dream, where landing the big client is the ultimate goal, and everything else be damned.

Kevin Spacey and Danny DeVito play Larry and Phil, two veteran sales reps who’ve been through the wringer more times than they can count. They’re at a convention, waiting in a hotel room to land the biggest fish in the pond, the elusive “Big Kahuna.” Along for the ride is Bob, a young, naive sales rep who’s about to get a crash course in the cutthroat world of sales.

The movie is basically one long conversation in a single room, but trust me, it’s not as boring as it sounds. Spacey and DeVito are at the top of their game, trading barbs and sales strategies like a couple of old pros. They talk about everything from the meaning of life to the best way to close a deal, and it’s all delivered with a healthy dose of cynicism and dark humor.

“The Big Kahuna” is a funny, thought-provoking look at the world of sales and the people who inhabit it. Just don’t expect any actual tips on how to close a deal – unless you count “find Jesus” as a viable sales strategy!

Tin Men (1987)

“Tin Men” is a sales movie gem that gives you a look into the sleazy but hilarious world of high pressure sales in 1950s Baltimore. Richard Dreyfuss and Danny DeVito play a pair of rival sales reps who get into an epic feud over a fender bender involving their precious Cadillacs. These “sales professionals” will do anything to make a buck, from scamming unsuspecting buyers with the “loss leader” to seducing each other’s wives. 

This sales movie captures the soul-crushing grind of being a sales rep. At its core, it’s a dark comedic look at the life of sales reps who have to lie to themselves as much as their prospective sales leads.

It’s a brutally honest but hilarious portrayal of the sales process and what it can do to a person’s psyche. A must-watch sales movie for any sales team looking for laughs… and sales lessons.

The Best Inspirational Sales Movies

Being a sales rep can straight-up suck sometimes. The grind of grinding out those cold calls. The frustration of a hot sales lead gone ice cold. The existential dread of wondering if you’re just a useless cog in some soulless corporate machine. It’s enough to make you want to quit.

But before you go living off the grid and embracing your new racoon wife, maybe watch one of these heartwarming sales movies that’ll remind you why you got into this racket in the first place.

So do yourself a favor and watch these inspirational sales movies. After all, if these guys could overcome being homeless, getting fired, and having to grovel to Rod Tidwell, your measly sales quota doesn’t seem so bad anymore, does it?

The Pursuit of Happyness (2006)

“The Pursuit of Happyness” is a rare movie that’ll make even the most jaded sales rep believe in the American Dream again.

Based on a true story, it follows the struggles of Chris Gardner (played by Will Smith in a powerhouse performance) as an unemployed medical sales professional trying to make it into a prestigious brokerage firm. While peddling portable bone-density scanners to uninterested doctors, Gardner has to juggle being a single dad and living on the streets with his son.

What makes this movie stand out is Will Smith’s raw, vulnerable portrayal of a man willing to sacrifice everything for a shot at a better life. You can’t help but root for him as he gets knocked down over and over but keeps getting back up. This movie will make you cry and laugh and everything in between. It is a true master piece of incredible storytelling and modern cinematography.

This movie is a harsh look at the soul-crushing grind. But it’s also an incredibly uplifting story about overcoming adversity through sheer force of will – something every sales rep can relate to on some level.

Jerry Maguire (1996)

“Jerry Maguire” is one of the best sales movies in my opinion. It will have you hugging yourself with delight, just like when a hot prospective lead finally signs on the dotted line. 

Tom Cruise plays Jerry, a slick, successful sports agent who has a crisis of conscience and writes a manifesto about putting clients first instead of chasing money. His unconventional sales practices get him canned, but the adorable Dorothy (played by Renee Zellweger) believes in him.

This sales movie has all the sales lessons you need – building genuine relationships with your target audience, staying passionate about your work, having an awesome sales strategy even when the pipeline dries up. Zellweger and Cruise have crazy chemistry, making you believe this unlikely duo can make it in the competitive world of sports agents.

The true gem is Cuba Gooding Jr. His and Cruise’s “Show me the money!” scene is legendary!

The Best TV Series About Sales

After a long day of getting chewed out by clients, fudging numbers, and struggling to hit those ever-increasing quotas, sometimes you just need to veg out with some top-notch TV series that really get what it’s like in the soul-crushing world of sales.

Whether you watch these with your sales team and bond over how accurate they are, or privately binge them while questioning your life choices, one thing’s for sure – these TV series about sales are like the perfect nightcap after another bruising day in sales.

White Gold (2017-2019)

If you loved The Inbetweeners’ cringe-worthy moments and juvenile humor, get ready for White Gold – a sassier take on the sales world from the same twisted minds. This BBC comedy follows Vincent (Ed Westwick), a cocky sales rep peddling windows in 80s Essex. 

Right off the bat, Vincent epitomizes the sleazeball salesman – breaking the fourth wall to brag about his sales skills and “perfect life” while lying through his teeth to everyone he meets (including his wife). Because that’s just how this obnoxious schmuck operates.

Backing up Vincent are his sales team misfits – the meek Lavender who can’t actually sell anything, and the aggressive Fitzpatrick rocking a greasy Begbie ‘stache. The constant alpha male posturing and chemistry between this mismatched trio is comedy gold!

While playing on sales stereotypes, the exaggerated yet believable characters feel taken straight from real life. But the true star is the era-defining 80s soundtrack that’ll have you tapping along to new wave bangers between laughs. White Gold delivers a fresh, dark comedic take on the sales world.

Ballers (2015-2019)

HBO’s “Ballers” is a TV series that’s gonna feel like it was ripped straight from your sales career. Starring the charismatic Dwayne “The Rock” Johnson (he’s actually acting Ok in this TV series), this show follows a retired NFL player named Spencer Strassmore. Strassmore is now a sales rep at a financial management company, trying to bring in prospective sales leads from the NFL ranks.

What makes “Ballers” so damn relatable is how it nails the sales struggles players face after blowing through their millions. From bad sales strategies with their money to dealing with unsuspecting buyers trying to mooch off them, these ballers need Strassmore’s sales skills more than ever.

But “Ballers” isn’t all about the successful salesman story. It gives you a real look at the gritty side of the sales game too. “Ballers” is a refreshingly honest take on the roller coaster sales career us sellers are strapped into.

House of Lies (2012-2016)

Look, if you’re some prude who can’t handle a few slurs and some skin, this Showtime sales TV series ain’t for you. House of Lies is an unapologetically crude comedy that doesn’t water down the harsh realities of the sales world.

The real star is Don Cheadle as the ruthless but charismatic management consultant Marty Kaan. Dude is a successful salesman sleazeball, but you can’t help rooting for him. Kristen Bell is fantastic as his pill-popping ex-wife too – a smart sales professional who’s also kinda crazy.

The writing is really sharp. Sure, some of the acting from the kid actors is a bit shaky, but who cares when you’re getting such savage sales lessons and sales gems?

The Best Sales Documentaries

As sales reps, we’re no strangers to a little… exaggeration. Overpromising, overselling, bending the truth until it nearly snaps – it’s all just part of the game… right? Well, these eye-opening sales documentaries take that to new levels.

Fyre (2019)

Many companies peddle useless stuff on marketplaces like Temu and Wish to make a quick buck. But this Fyre Festival fiasco? That’s a whole new level of scamming.

Billy McFarland was pitching a fantasy “Woodstock for Millennials” to the models, influencers, and trust fund kids. Dude had major sales skills, I’ll give him that. He managed to con everyone from Kendall Jenner to Ja Rule into shilling this non-existent music fest in the Bahamas. 

So what was Billy’s sales strategy? Pure Instagram smoke and mirrors. A few slick promotional videos showing bikini-clad supermodels dancing on a paradise island was all it took to get the FOMO-stricken masses opening their wallets.

In the digital age, perception is everything in the marketing industry. If you can make the mirage look real enough on social media, you can sell just about anything to people desperate for the illusion of a better life. This documentary lays bare the vanity and stupidity that fueled this epic con job.

The Inventor: Out for Blood in Silicon Valley (2019)

“The Inventor” will make you question every sales pitch you’ve ever given. This “sales documentary” takes us down the twisted trail of Elizabeth Holmes and her fraudulent biotech startup Theranos. 

Holmes was the ultimate smooth-talking hustler who sold the Bay area on a revolutionary blood testing machine that was basically a $10 billion lie. She swindled some of the biggest names in politics and business to invest in Theranos. But despite Elizabeth’s Oscar-worthy performance, turned out her miracle machine couldn’t actually do jack squat. The entire thing was a house of cards that put people’s health at risk.

What makes “The Inventor” a must-see sales film is seeing how far one was willing to take the sales game. She had no real product, just empty promises and next level sales skills.

About the Author

Team at DeckLinks provides industry-leading thought leadership on B2B sales and marketing, lead nurturing, and sales enablement strategies. With decades of combined C-suite and VP-level experience, they deliver actionable B2B sales and marketing content that gives B2B companies a competitive advantage. Their proven insights on lead management, conversion rate and sales optimization, sales productivity, and tech stack empower companies to increase revenue growth and ROI.