5 great movies to watch on HBO on Valentine’s Day 2020

What movies to watch on HBO for Valentine’s Day? We picked some great movies to watch, including the Thomas Crown Affair and Working Girl.

HBO has tons of great movies to watch Valentine’s Day, which can make it difficult to choose what to watch.

Don’t worry, we picked five good movies to watch on HBO for Valentine’s Day 2020, so you don’t have too much trouble finding a good movie to watch.

5. The Thomas Crown Affair (1999)

This isn’t your typical Valentine’s Day movie which is why I love it.

Meet the suave, sophisticated billionaire Thomas Crown superbly played by Pierce Brosnan. With all that money, there isn’t much Crown cannot buy or entice. It’s not surprising he is bored with how easy everything comes to him and resorts to pushing the boundaries by stealing a priceless painting from an art gallery.

The insurance company sends the beautiful Catherine Banning (Rene Russo) to find and return said painting. It quickly becomes apparent that Catherine is the female version of Crown. The two are involved in a high-stakes game of cat and mouse. What neither of them expects is they fall for each other hard in the process. Too far into the game, neither knows if it’s real. Does Catherine really love Crown or is she just trying to get the painting?

Does Crown truly love Catherine, or is he just trying to stay out of jail?  In the middle of all of this, a policeman Michael McCann (Dennis Leary) is trying to recover the painting and arrest Crown. The story plays out against the backdrop of gorgeous scenery while you’re secretly hoping Crown and Catherine get together. Do they? You will have to watch and see, but it is so worth watching.

4. Working Girl (1988)

Working Girl tells the story of a young New York City receptionist, Tess McGill (Melanie Griffith), who is trying to better her situation. She is ambitious and intelligent but is having problems with people taking her seriously. In a bar scene with Jack Trainer (Harrison Ford), McGill summed up her problem in one sentence:  “I have a mind for business but a bod for sin.”

In Katherine Parker (Sigourney Weaver), McGill thinks she’s finally found a mentor. Another woman who understands the situation and willing to teach her the ropes. Unfortunately, McGill learns that Parker stole her idea about having a client, Oren Trask (Philip Bosco), buy into radio. Naturally upset, she leaves work early and goes home only to find her boyfriend Mick Dugan (Alec Baldwin) in bed with another woman.

Tired of being nice, McGill learns Parker is holed up from a skiing accident and decides to make the merger happen with Trask Industries. Enrolling the aid of Trainer, they put together an acquisition merger between Trask Industries and a radio company. Meanwhile, a budding romance is developing between Tess and Jack and everything is going well until Parker finds out and shows up at the meeting.

What happens next? This a really good movie about chasing one’s dreams which sometimes means making your own rules.

3. Grosse Pointe Blank (1997)

This is definitely not your typical love story, but I loved it because of the unusual storyline, and John Cusack did a great job portraying Martin Blank.

Blank is a hitman who is re-evaluating his life and purpose. His secretary, Marcella (Joan Cusack), received an invitation for Blank to attend his 10-year high school reunion. She takes it as a sign for him to go home, but Blank resists until an assignment comes in for his home town, Grosse Pointe, Michigan.

Once he gets there, he delays completing the hit and wants to get in touch with his ex-girlfriend, Debi Newberry (Minnie Driver). Blank stood Debi up on Prom night and disappeared without a trace. He finds her, and after a rather awkward meeting where he can’t explain where he was for the last 10 years, he leaves. Then, he goes back because the attraction is still there for both of them, and he invites her to the reunion.

Blank is interested in restarting with Debi, but things get complicated when another hitman shows up. Then, Grocer (Dan Ackroyd), who is trying to set up an assassin, is chasing Blank to join or die. When Blank turns the offer down Grocer turns him over to two NSA operatives who are also trying to kill him. If that wasn’t enough, Blank’s target is Bart Newberry (Mitchell Ryan) who is Debi’s father.

Will Debi and Martin get back together? This is a fun and entertaining movie to watch and find out.

2. Stakeout (1987)

This is a great movie to watch. It’s hilarious and romantic at the same time. Two police partners, Chris Lecce (Richard Dreyfuss) and Bill Reimers (Emilio Estevez), team up with another team for a stakeout. Each team does a twelve-hour shift, and Lecce and Reimers entertain themselves by playing practical jokes on the other team. Of course, they respond back and the responses are funny.

The two teams are staking out Maria McGuire (Madaleine Stowe), who is the ex-girlfriend of Richard ‘Stick’ Montgomery. Montgomery is an escaped convict, and although the odds are slim, the police are staking out Maria. In the process of the stakeout, Lecce accidentally runs into McGuire at a grocery store. A budding romance stems from that meeting, and Lecce pursues the romance against Reimers’s advice.

1. Hope Floats (1998)

This is a true romantic movie, but it is also about rediscovering yourself after heartbreak.

Birdee Pruitt (Sandra Bullock) is humiliated on live TV by her best friend Connie (Rosanna Arquette). She tells Birdee that she is in love with Birdee’s husband, Bill (Michael Pare), and they have been having an affair.

Birdee returns to her home town with her daughter, Bernice (Mae Whitman), hoping to recover. Except, Birdee lost herself in the marriage and doesn’t know who she is outside of the marriage.

To make matters worse, old female acquaintances are reveling in the fact that Birdee returned in disgrace. Bernice blames Birdee for the marriage falling apart and the reason her daddy left them.

Justin Matisse (Harry Connick, Jr.) who has had a crush on Birdee since high school, comes into her life. With kindness and patience, he slowly breaks through Birdee’s hurt and love begins to blossom.