The Business of Love: 5 Movies To Watch Where The Bottom Line Is Romance

Valentine’s Day is fast approaching and while you may or may not be contemplating a gift of roses, flowers or champagne, you may also be thinking about the gift of a romantic movie.

Last year, I asked my Facebook friends to name their favorite romantic movies, thinking I would get a few answers. Au contraire, as when I was done putting together the list, I had more than 140 movies.

There are a number of sub-genres of romantic movies, with rom-com as the most popular. As Benzinga is a business media site, I decided to select films from the list which had a central business theme or a major business subplot.

Who says love and money don’t mix?

Working Girl (1988): This movie is about a working-class, Staten Island David (Melanie Griffith) versus a wealthy, Upper East Side Goliath (Sigourney Weaver) with the winner getting the business deal and M&A genius Jack Trainer (Harrison Ford). 

The film features stellar performances by Weaver, Griffith and Ford, the latter of which shows his underutilized comedic skills and charm. Among the many classic lines include, “I have a head for business and a body for sin. Is there anything wrong with that?” (You'll have to watch the movie to see who uttered that.)

The movie is also a great snapshot of Wall Street and New York City in the late 1980s. Yes, the hair was that big, the make-up bold and women wore those Reeboks to work, then changed into high heels when they got to work.

The Thomas Crown Affair (1968) and (1999): Wealthy Boston businessman Thomas Crown decides to pull the perfect art heist. Well, maybe, as he has insurance investigator Vicki Anderson on his trail. Does she catch him? Or does she capture his heart? Does either of them go to jail?

The original version of the film starred Steve McQueen as Crown and Faye Dunaway as Anderson. It also saw these actors at the beginning of their heyday: McQueen’s “Bullitt” was about to be released, and Dunaway had just come off the success of “Bonnie and Clyde.”

Among the other highlights is Boston as the backdrop, and the scene where McQueen and Dunaway play chess is considered a classic instruction in flirtation.

The 1999 version starred Pierce Brosnan, in the middle of his James Bond years, and Rene Russo, who was more known for her roles in comedy or action films. The plot is still the same, though Russo’s character is named Catherine Banning, and it is set in New York City and Martinique. Dunaway played a small role as Brosnan’s psychiatrist.

Two Weeks Notice (2002): Starring Hugh Grant as a billionaire developer playboy, Sandra Bullock is the activist attorney he hires. Sparks fly, of course. But will love last?

It all comes down to what is called the Coney Island Community Center in the film. I won’t reveal what happens, but in real-life the Spanish Revival building constructed in 1923 for Childs Restaurant was declared a New York Landmark a month after the film’s premiere. It was eventually renovated with an amphitheater and is now called Ford Amphitheater at Coney Island in Brooklyn, New York.

You’ve Got Mail (1998): Tom Hanks as a millionaire playboy who is part of a family-owned book chain, while Meg Ryan is the owner of a small children’s bookstore that may go out of business. They meet online in an AOL chat room and fall in love, not having met or known anything about each other’s businesses.

The title comes from the greeting that AOL (remember that!) users received when they got an email. It also harkens to a time when bookstore chains (pre-Amazon) threatened to put small bookstores out of business.

Baby Boom (1978): Starring Diane Keaton as a high-powered businesswoman who inherits a baby, moves to Vermont, renovates a decrepit farmhouse, starts a baby food business and falls in love with veterinarian Sam Shepard.

When New York comes a calling, will the city win over country living?

Of note, it is fun to see James Spader in all of his early career bad-boy gloriousness as Keaton’s assistant who stabs her in the back (business-wise, of course). 

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Honorable Mentions: While not in my top five, these following films make good movie and romantic business sense!

How To Lose a Guy In 10 Days (2003): Starring Kate Hudson and Matthew McConaughey. Ad executive falls for magazine writer — both have ulterior motives.

Elizabethtown (2005): Starring Orlando Bloom and Kirsten Dunst, whose character was what inspired the term “Manic Pixie Dream Girl,” coined by film critic Nathan Rabin. Bloom’s character designed a sneaker that was a catastrophic failure for a company that suspiciously reminds you of Nike.

Wall Street (1987): Yes, it’s a love story! A working-class boy, Charlie Sheen, leaves his life behind, dazzled by the Wall Street mogul Michael Douglas (aka Gordon Gekko in the movie), and in a sense, falls in love with the man and the lifestyle, only to find it shallow and illegal. Finds out greed is not good, but does he find redemption or a jail cell?

Pretty Woman (1990): The movie that made Julia Roberts a star. The setting is Los Angeles and Roberts' character plays a prostitute (with of course, a heart of gold), while corporate raider Richard Gere hires her for his stay during a big business deal.

Besides the love story, "Pretty Woman" has what fellow Benzinga Editor Anthony Noto says, “One of the few movies that depict private equity culture.”

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Photo: Paradise studio via Shutterstock