$15 Bounty: A new CEO struggles to run his company but an old bartender gives him advice that turns things around

Hello everyone,

Some 20 years ago I watched an excellent movie that I now have only a few memories of.

A young man in his 30s becomes the new CEO or a high-ranking manager of a company, but he is too nice and kind so he struggles to make an impact. The old guard at the company disrespects him, new employees are afraid to support him, so he becomes depressed as everyone takes him for a joke.

One night, he is at a bar and opens his heart to an old bartender who runs the place. The bartender decides to help him and starts advising him on what to do and how to behave. He tells the manager first to fire or move to other subsidiaries many of the older employees so they will no longer be a thorn in his side, and also to promote many of the newer employees so that he will have a huge number of loyal and grateful people working for him.

There is also a scene that is etched on my memory. One of the main troublemakers for the manager is an older man who was maybe overlooked for a promotion when the protagonist was hired, but he still runs the company from the shadows and undermines the manager. He has a beautiful mistress, a girl who is maybe his secretary and also his lover. There is one scene where they are at his mansion and are in the pool. The older guy tells her he loves her, she replies that he loves the sex with her and the crazy stuff she does to him, not her.

I am mentioning this because when the bartender instructs the manager to fire/move on the troublemakers, the older guy is given his marching orders, but so is the girl. However, at a company party, where many of the promoted employees have gathered, she shows up determined to keep her job. She waits until the manager goes to the restroom and follows him in. She starts coming on to him, and pretty soon she’s kissing him and she climbs on top as he sits on the toilet. I remember that she asks him: “Do you want me?” repeatedly as she kisses him, and when he finally says: “Yes,” she stops and says: “Then don’t let them fire me,” and walks out. I am not sure about the exact words she uses when she demands that he saves her job, but I am certain she asks him twice if he wants her and then stops kissing him and tells him to save her job. I do not remember what happens afterwards.

Sadly, I don’t remember the actors’ names or anything like that, but if I watched that movie circa 20 years ago, my best guess is it was made in the 90s.

If anyone is familiar with it, I would really appreciate any help.

Thank you,
Jain

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Not sure if it is correct as it doesn’t match all the way, but the only movie coming to mind is Mr. Destiny. It is about a guy feeling stuck in his life and a bartender changes his life. I haven’t seen it in many years so I’m not sure on the specific scenes or not.

Extract?

@Jain

The movie you are describing may be called “Swimming with Sharks” (1994). It stars Kevin Spacey as the new, kind-hearted, and naive assistant to a powerful Hollywood executive, played by Frank Whaley. The old guard at the company disrespects him, new employees are afraid to support him, and he struggles to make an impact.

He confides in the bartender, played by Benicio Del Toro, who advises him to assert himself and not be afraid to take charge. He follows the bartender’s advice, fires some of the old guard and promotes the newer employees. However, he goes too far and becomes just as ruthless and cruel as his boss.

The scene you described with the older man and his mistress is a pivotal moment in the movie. The girl is played by Michelle Forbes, and her character’s name is Dawn Lockard. The manager fires her along with the older man, but she shows up at the company party and seduces him in the restroom, asking him repeatedly if he wants her. When he finally says yes, she tells him not to let them fire her.

The movie is a dark comedy and a critique of the Hollywood system, with Spacey’s character representing the idealistic newcomer who is corrupted by the industry.

Could be “The Secret of My Success”.

Have a look at this list Sort by Popularity - Most Popular Movies and TV Shows tagged with keywords "bartender", "ceo" - IMDb I refined the search to movies before the year 2000 and used keywords ‘ceo’ and ‘bartender’, IMDB came up with 6 titles.

What about Wall Street? I recall the main character trying to be good at his job and he struggles but he isn’t a CEO and people just don’t take him real serious. He gets in over his head and his dad meets him at a bar where he talks to him about his job and doing things some kind of way. It’s a long shot but I thought I would suggest it while I still try to figure it out if this isn’t it. I believe a woman in white seduces the Charlie Sheen character at one point also.