8. Groundhog Day
Directed by: Harold Ramis
Starring: Bill Murray, Andie MacDowell, Chris Elliott

Image Credit: Columbia Pictures
When Phil, a TV weatherman working for a local station in Pennsylvania is sent on assignment to cover Groundhog Day festivities in Punxsutawney, he certainly gets more than he bargained for. The arrogant weatherman is convinced he’s made for national news stardom despite treating his co-workers with contempt, especially his producer Rita. When a freak snowstorm strands him in the small town, he wakes up the next morning with a case of déjà vu. The next morning it happens again, and again, and again. No matter what he does—imprisonment, attempted suicide, kidnapping the groundhog—he’s still stuck with Groundhog Day. As he’s forced to relive the day, he is forced to look at everyone around him and re-evaluate his life and role in it. He begins to care about others and actually respect people. While he’s at it, he’s developing feelings for his producer, Rita but it’s a vicious cycle and one he can’t get out of. Or can he?
Why It’s Great for the Guys: This is an all-around lovable movie that many don’t see as much of a romance but more of a seasonal tradition, similarly to viewing It’s A Wonderful Life as a real Christmas movie in contrast to a holiday favorite. In all fairness, it really should be watched during any time of year. The film has been on four of AFI’s best lists; was added to the United States National Film Registry in 2006 as “culturally, historically, or aesthetically significant”; and stars Bill Murray (that’s reason enough). With that in mind, Groundhog Day is funny and philosophical, and with regard to Valentine’s, is really a film about a selfish man learning to truly love someone other than himself. We all get tied up with work and success, sometimes films like this really are eye-openers. Through the time Phil spends repeating the day over and over, he develops an established and heartfelt relationship with Rita because time is really on his side (something we wish we all had more of). He’s able to relive everyday and find his best self with her, which transforms his surface-like feelings to something more honest and genuine.
9. Jerry Maguire
Directed by: Cameron Crowe
Starring: Tom Cruise, Renee Zellweger, Cuba Gooding Jr., Bonnie Hunt

Image Credit: The Weinstein Company
Jerry Maguire is an enthusiastic and successful agent in a major sports management firm, but also happens to be someone who has lost his heart amid the chaos in business. After a troubling encounter with the son of an injured athlete he represents, Jerry has a serious moral epiphany and writes a memo, calling on himself and co-workers about the long-term welfare of clients and work less on immediate profiteering. Jerry is then fired but joined by staff accountant Dorothy, a single mother secretly in love with him. As the two venture out in their newfound business together and fall in love, they recruit Rod Tidwell, a football player whose potential for the game has been dampened by his extreme pride and arrogance. Rod soon becomes Jerry’s ultimate client and one he will never forget.
Why It’s Great for the Guys: For obvious reasons, the backdrop of football could be one argument but that’s too simple. This film is great because though it may be structured as a romance, bordering dramedy, it is a film about relationships not just between Jerry and Dorothy, but Jerry and Rod who showcase a very tight and loving bromance. It’s only when Rod as Jerry’s friend points out the weak spots in Jerry’s relationship with Dorothy, that Jerry finally becomes the man he needs to. This film is a lot about friendship in that sense and in many ways, he and Rod complete each other.
10. Intolerable Cruelty
Directed by: Ethan and Joel Coen
Starring: George Clooney, Catherine Zeta-Jones, Tom Wilkinson, Geoffrey Rush

Image Credit: Universal Pictures
Miles Massey is a high powered LA divorce lawyer with a mid-life crisis, representing one of the wealthiest men in the State, Rex Rexroth. Miles meets his match in Rex’s ex-wife Marilyn, a gold-digger straight out of a Kanye West tune. While Miles is impressed with her and becomes attracted to her ways, he still manages to defeat Marilyn in court for his client, upsetting her a great deal. It is then that she decides to play on his emotions, getting her own revenge on what was ‘rightfully’ hers. The two engage in a ruthless romantic pursuit to out-swindle one another, while falling in love.
Why It’s Great for the Guys: First of all, this is a Coen Brothers film—I think that says enough. Secondly, it’s a romantic comedy that is somewhat reminiscent of old Hollywood screwballs, peppered with a just a pinch of the dark comedy touch known by the Coens. The film’s tone is comical with Clooney portraying a Cary Grant type character seen in Arsenic & Old Lace, and the quirkiness of Coen humor popping into more dark intense scenes for added drama and effect. It’s a thorny topic that the film hits on but definitely hits the right rhythm with wacky casting. It’s not like any of the other romantic comedies as it’s sharp, zany and the last hilarious piece of work from the Coens since Raising Arizona.
11. The Town
Directed by: Ben Affleck
Starring: Ben Affleck, Rebecca Hall, Jeremy Renner, Jon Hamm

Image Credit: Warner Brothers Pictures
Adapted from Chuck Hogan’s novel, “Prince of Thieves,” The Town finds Boston bank robber, Doug MacRay falling for bank manager, Claire after his gang had previously taken her hostage during a heist. Doug had every chance in his life to walk the straight and narrow path, but chose to be part of the most ruthless gang in Boston. Over the years, his partners in crime have become somewhat of a family to him, especially Jem who just so happens to be the most dangerous of them all. As the FBI turn up the heat on the gang, Doug finds himself falling for Claire through a forged chance meeting, while searching for a way of cutting his ties to his criminal past. However, Jem begins to grow increasingly suspicious of Doug’s true intentions. Now caught between two worlds with no chance of turning back, Doug realizes that his only hope for finding a happy future is to betray the only family he’s ever known.
Why It’s Great for the Guys: The Town doesn’t seem like a romantic movie in any facet. In fact, it’s extremely dark and gritty. It doesn’t really shine much hope for romance, but that’s just on the surface. Deep down, this movie is very intense in content and romantically dreamy at times, particularly the ending. It has superb casting and a very tense story. It’s driven as an action film with drama and romance on the side, but just enough to keep you on the edge of your seat. The thrills and suspense is reminiscent of the old school heist films, but a little more sharper. It is however, arguably, one of the best heist movies from the last decade. Affleck really knows how to deliver great films and this is one of them.
12. Big Fish
Directed by: Tim Burton
Starring: Ewan McGregor, Albert Finney, Helena Bonham Carter

Image Credit: Columbia Pictures
Based on the book, “Big Fish: A Novel of Mythic Proportions” by Daniel Wallace, the Tim Burton fantasy film finds a young man named William who gets to know his dying father, Edward. Edward is known for telling tall tales about his life, what he experienced growing up, how he met his wife, and all the adventures he came across. During Edward’s last days, William and his wife hold a bedside vigil as the dying father recollects memories of his youth. Though still doubtful of his father’s famous folklore and legends, William decides to get to the bottom of his father’s life and makes a journey to meet the mysterious woman from whom his father had bought property from.
Why It’s Great for the Guys: The film is probably one of Tim Burton’s best. It’s subtle in film-making and charming at that. The fantasy sequences may be depicting all these legends of a dying Edward but the reality is, they are very much of our own world. The father-son dynamic is sweet and something a few men can identify with. There is so much insight and conviction in such a relationship, that it will resonate far deeper than any declaration that life is “one big dark room” as per the philosophy found in a film like Beetlejuice. Edward and William are strained, but there’s a lovely sort of understanding that develops between the two of them and translates perfectly to the viewers. It’s so touching and bittersweet, and honestly, will even make the tough guys cry.
13. The Apartment
Directed by: Billy Wilder
Starring: Jack Lemmon, Shirley MacLaine, Fred MacMurray

Image Credit: United Artists
Directed and co-written by Billy Wilder, The Apartment is a timeless classic. The film, way ahead of its time, depicted the cold take on the sex-and-money atmosphere of the workplace, and how educated employees can sometimes be treated like (and feel a lot like) tools in order to achieve their own success. Starring Jack Lemmon in the lead, The Apartment finds C.C Baxter, a go-getting office worker who loans his tiny apartment to philandering superiors from work for their romantic trysts. After becoming smitten with Fran Kubelik, an elevator operator, C.C finds out she’s his callous boss’ mistress and has a hard time concealing his feelings or even getting over the bright-eyed Fran.
Why It’s Great for the Guys: Men will appreciate this movie for Jack Lemmon’s character and the men’s room type humor. If you like Mad Men, you will like this one for sure. It isn’t exactly a cheerful film at all. Just because it’s in black and white doesn’t mean the content is subdued. No, not at all. It’s dark at times and though funny, it’s not hilarious but more truthful and heartfelt. It’s an interesting look at the workforce and extra-marital affairs; while being a small character study into what it really means to be loved, and what it looks like to take care of someone you know is going through a rough time in life.
14. The Wedding Singer
Directed by: Frank Coraci
Starring: Adam Sandler, Drew Barrymore

Image Credit: New Line Cinema
Set in 1985, Robbie Hart is a down-on-his-luck singer whose rock band is unable to make a name for themselves. As he makes a living playing wedding receptions while holding on to the dream, he is able to create a steady income for himself. While singing at a reception one night, he meets and befriends waitress, Julia Sullivan. Despite being engaged, Robbie takes a liking to Julia and learns she is engaged too, unfortunately though, to an obnoxious, self-obsessed yuppie named Glenn Gulia. Glenn is consistently disrespectful and unfaithful to Julia while she unknowingly plans her wedding. As Robbie’s fiance breaks off their engagement, he soon realizes his true feelings for Julia and how he must step in to stop her from marrying Glenn and becoming….’Julia Gulia’!
Why It’s Great for the Guys: You need a laugh-out-loud comedy for Valentine’s and this one is the best option! The comedy shenanigans of Sandler and company is sure to deliver in this romantic comedy that is fun for both men and women. Sandler’s films from the late 90s brought around great laughs and schmaltzy humor that will bring a smile to your face. This one is a gem with a great soundtrack, as well as hilarious and memorable dialogue. Though the plot is simplistic, it is cute and the gags are consistently funny, particularly for those who grew up in the 1980s and suffered through questionable fashion decisions.
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Hopefully these films will be something great that everyone can watch, either alone or with your significant other. However if you decide to spend the night in with Netflix, hopefully you will have it exactly the way you want. I know I’m suppose to say the takeaway from Valentine’s Day is to love yourself first, then love others and ‘yada, yada’, but the day is about enjoying what life has to offer. While you’re at it though, don’t forget to visit CVS or your local pharmacy and pick up some last minute cutesy boxed chocolates for your loved one or just yourself. There’s no shame in eating a whole box on your own.
Happy Valentine’s Day!
What are some of your favorite films to watch on Valentine’s Day? Let us know in the comments below!
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