Why “Cocktail” is One of the Greatest Sales Movies Ever Made


When you think about great sales movies, the obvious choices like “Wall Street,” “Wolf of Wall Street,” “Boiler Room” and the like are typically the first to come up. Not many would immediately think of 1988 multiple Raspberry award-winning film “Cocktail” – but I do. For multiple reasons.

For many, if they have seen it at all, “Cocktail” exists as that silly, Tom Cruise flair bartending flick from the 80’s – with an 80’s soundtrack to boot. I often ask bartenders if they’ve seen the film, even finding an establishment once with a drink called “Coughlin’s Law” where I had to educate the staff on this gem.

A great sales movie requires a few things: The protagonist, ambitious and clearly ready to take over the world, embarking on a journey to greatness with stumbles and hard work upon the way. A killer soundtrack. A mentor figure. Valuable lessons that we can apply in our own lives. “Cocktail” has them all.

The film opens as Brian Flanagan (a young Tom Cruise, post- “Top Gun” and “The Color of Money”), fresh out of the military, hitches a ride on a bus heading to New York City. If you can make it there, you can make it anywhere. While on this seemingly long trek, he is consuming a book entitled “How to Turn Your Idea Into a Million Dollars.” They come up around the bend and we see the glorious World Trade Center. He tells a young kid sitting next to him, “Someday we’re going to own that town.”

He’s determined and has clearly stated goals to “make a million.”

He immediately reaches out to his “network” – his Uncle Pat, who is full of words of wisdom and even says he’ll get him into a job that Flanagan feels he’s better than. Haven’t we all been there? We don’t want to settle just yet.

“Every man wakes up one fine morning with a wife and kids. Where’d they come from? They weren’t here last time I looked. Most things in life – good and bad – just sort of happen to you,” Uncle Pat waxes poetic. “You don’t get rich giving things away.” “

“Outwork, outthink, out-scheme and out-maneuver. You make no friends. You trust nobody.” And you make sure “you’re the smartest guy in the room whenever the subject of money comes up.” These are the words of the jaded “father figure” who has his own business and who is the extent of Brian’s small network to begin with.

Flanagan quickly hits the job circuit. He immediately heads to Wall Street, believing that his excited demeanor and go-getter attitude will land him a job. Not so. For a gig on Wall Street, for an advertising role on Madison Avenue – he’s told he does not have a degree or the credentials. No one will hire him without a degree or experience and he is given the typical blowoff lines like “maybe in 6 or 8 months”.

So, he not only enrolls in city college but he happens across a “Help Wanted” sign at TGI Friday’s and as fate would happen he enters the establishment. The aging bartender immediately tells him the “bar’s closed.” They begin a dialogue whereby Brian reveals he is looking for a job. Anything else.

Enter Douglas Coughlin, self-proclaimed “logical negativist” who has propounded a set of laws the world generally ignores, to its detriment. The first one? Coughlin’s Law: “Anything else is always something better.”

Think about the genius here: how often are we examining another job or set of circumstances, thinking, “if I only had that, I’d be happy.” We spend far too much time thinking something else would be superior to our current situation rather than investing in ourselves and in our path. Those investments would lead to dividends if only we saw them through. Many of us need only to adjust the sails and continue on our course for smoother waters.

And despite the fact Flanagan really has zero credentials to be a bartender at TGI Friday’s, he’s given a shot. And thus begins a dizzying rise to the top.

It starts shakily. Like any new role, Flanagan comes in and falls on his face. How many times have we begun a new role and felt unprepared, fighting a losing battle and feeling like our co-workers and customers disliked us or laughed at our lack of credentials or experience? Despite this, Coughlin takes a liking to his determination and grit and offers him the job. It’s only a matter of time before Brian gets the hang of it, and he’s able to mix his wit and charm with growing flair bartending skills: a killer cocktail.

His schooling journey continues, as he is convinced his real career lies elsewhere, but Flanagan laments that nothing learned in his classes makes a difference in the street. Coughlin’s reply? “If you know that, you’re ready to graduate.” How much did your schooling prepare/not prepare you for the lessons that were to come in your career?

It’s only a matter of time before Brian sees that there is potential for the two of them to embark on their own business venture. Coughlin is the skeptic. They are given another opportunity at a different bar as the headliners because of their unique approach and charisma – which is so indicative of how things work in the real world. You can think and believe that your career will take a certain course. You can apply for roles and be shot down. However, if you follow your talents and shine, the real opportunities will come from being noticed for standing out and for persevering in the roles where you pay your dues.

The mentor-protégé relationship breaks down over a woman, of course, and Flanagan’s growing persona. He hightails it to Jamaica where he opens his own bar, serving Kevin’s uncle from “Home Alone” and the erstwhile Jim Walsh from “Beverly Hills, 90210” after the Beach Boys deliver the musical magic that is “Kokomo.” He jumps in to help a girl who is sick and dehydrated on the beach, and inadvertently meets Jordan – the female lead, and “Karate Kid” alum Elisabeth Shue.

He judges her book by its cover: just a girl who’s a tourist in Jamaica, and, while they have a good time together and she is supportive as he laments how far away from his dreams he feels he is, he takes the relationship for granted. Brian succumbs to being tempted by an extremely wealthy woman who can seemingly offer him everything he thinks he wants: a high profile sales job back in New York and a “better quality of life”. He follows this path to much chagrin, realizing that the path he chose was not fulfilling. This potential path of money and parties and this sales career was not true to what did fulfill him, which – like for many of us – turns out to be love and family. What he truly wanted and needed – a career he enjoys using his natural talents and charms, and the love of Jordan (who turned out to be rich anyway) – was right in front of him. Brian realizes his failure, and requires a second chance (which we all need from time to time). He also adjusts his strategy and decides to go back to work for Coughlin so he can support an unexpected child. We’ve all made decisions based on what’s right for our family and our shifting priorities.

Jordan has a story as well – she sets out to make it with her own talent and artwork rather than follow on the coattails of her wealthy family. She is supportive of Brian but works at a diner to support herself while leaving time for her “side hustle” of painting in hopes she can make it in that arena someday.

Another impactful Coughlin’s Law: “Never show surprise, never lose your cool.” This is applicable in any situation, as our reactions can often be our undoing. From responding poorly to a customer objection or unforeseen catastrophe that causes a deal to go awry, it’s our ability to shift and pivot which will get us back on track – not making some drastic move or showing our strain. Take everything in stride, and act as if you knew the objection was coming and that the potential deal-breaker could happen. It minimizes fallout.

The back half of this film suffers. Really, as soon as we see Doug Coughlin with wife on the beach, the lessons stop and the protagonist starts making foolhardy decisions in an attempt to impress his mentor. We all go through these spells – we step out of the tried and true process and the winning formula that got us to the top. We second-guess ourselves, do not stay true to the fundamentals and we take for granted those who genuinely care about us.

Doug Coughlin seemed like he was genuinely enjoying his life when he found Brian Flanagan and was able to impart his knowledge and teach these lessons he had learned. Always chasing this dream of “making it big” and tapping into the wealth around him via a “rich woman with nothing to do with their money,” Coughlin found this existence to be far more difficult than he envisioned. He opened his own place – had a great idea – but it faltered when it came to the day to day business decisions. He lost everything buying stock on margin to attempt to recover, and floundered in his desperation. In the end, he realizes he knew relatively nothing and that he should have stayed true to his best friend in the world.

“Cocktail” shows us players like Brian, Doug and Uncle Pat at various stages in their lives and career, and the evolution of Brian Flanagan from school to first job to business owner and entrepreneur. That journey is not without failures and stumbling, but through the bad decisions he makes he realizes the people and principles that he needs established as foundation as he embarks on his true calling. “Everything ends badly, or else it wouldn’t end.” Each ending in Flanagan’s career leads to new beginnings; the result of which was nowhere near what he initially envisioned – which is how every great success story truly plays out.

As Doug Coughlin tells us, “”There are two kinds of people in this world, the workers and the hustlers. The hustlers never work and the workers never hustle.”

If you’re looking for a great sales film you’ve likely never seen or haven’t seen in a while, check out (at least the first half of) “Cocktail”! It’s visually stimulating and immediately quotable. You’ll laugh, you’ll learn and at the very least you’ll leave entertained.


Carson V. Heady has written a book entitled “Birth of a Salesman” and sequels “The Salesman Against the World” and “A Salesman Forever” which take the unique approach of serving as sales/leadership books inside of novels showing proven sales principles designed to birth you into the top producer you were born to be. If you would like to strengthen your sales and leadership skills, go to https://www.amazon.com/dp/B073HN3SXQ

Heady posts for “Consult Carson” serving as the “Dear Abby” of sales and sales leadership. You may post any question that puzzles you regarding sales and sales leadership careers: interviewing, the sales process, advancing and achieving.

Question submissions can be made via LinkedIn to Carson V. Heady, this Facebook page: https://www.facebook.com/pages/Carson-V-Heady/125078150858064?ref=hl , Twitter via @cvheady007 or e-mail at cvheady007@yahoo.com or you may post an anonymous comment as a reply to my WordPress blog at the bottom of this page: https://carsonvheady.wordpress.com/the-home-of-birth-of-a-salesman-2010-published-by-world-audience-inc-and-the-salesman-against-the-world-2014/


About cvheady007

I am a Christian, Husband, Dad, workaholic and author. Biography Carson Vincent Heady was born in Cape Girardeau, MO, graduated from Southeast Missouri State University and moved to St. Louis in 2001. He has served in sales and leadership across Microsoft, AT&T, Verizon and T-Mobile. Carson is best-selling author of the Birth of a Salesman series, the first book of which was published by World Audience Inc. in 2010. He released The Salesman Against the World in 2014, A Salesman Forever in 2016 and Salesman on Fire in 2020. He is also featured in Scott Ingram’s B2B Sales Mentors: 20 Stories from 20 Top 1% Sales Professionals. Carson is a 7-time CEO/President’s Club winner across 5 roles at AT&T and Microsoft and National Verizon Rockstar winner. He has been recognized as a top social seller at Microsoft and is consistently ranked in the top 25 sales gurus in the world on Rise Global. He is included among the Top 50 sales authors on LinkedIn. With over 330K social followers, Carson has also been interviewed on over 30 sales and leadership podcasts, by such luminaries as Jeffrey & Jennifer Gitomer, Jeb Blount, Brandon Bornancin, Sam Dunning, Larry Levine, Darrell Amy, Scott Ingram, Thierry van Herwijnen, Jim Brown, Sam Jacobs, Luigi Prestinenzi, Donald Kelly, Marylou Tyler, George Leith, Pat Helmer, Eric Nelson, Ron Tunick, Jeff Arthur, Mary Ann Samedi, Jean Oursler, Andre Harrell, Marlene Chism, Bill Crespo, Matt Tanguay, Josh Wheeler and Chad Bostick. He has also co-hosted the Smart Biz Show on EG Marketing Radio. His articles have appeared in several noteworthy publications such as SalesGravy, Smash! Sales, Salesopedia and the Baylor Sports Department S3 Report. Carson lives in St. Louis, MO, with his wife Amy and daughters Madison, Sidonia and Charlotte.
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