Due to popular demand – and to help “celebrate” Valentine’s Day – Art House Film Wire is back with another 10 GREAT bad-relationship movies. We love these 10 fantastic flicks but don’t adore their on-screen couple’s behavior. Ten life lessons, perhaps, or for the singles out there, 10 reasons stay solo for a while. (and here’s our first article: 10 Great Bad-Relationship Movies!)
10. “Tootsie” (1982) – Michael Dorsey is a New York City actor who can’t find work, but he dresses up as a woman named Dorothy Michaels, and what do you know, he lands a spot on the TV soap opera “Southwest General”! Is it always that easy? Anyways, in addition to living most of his waking hours as a woman, he starts a relationship – as a man – with his long-time acting friend, Sandy (Teri Garr), and finds himself awfully attracted to his new female co-star, Julie (Jessica Lange). Michael doesn’t find the time for Sandy and regularly blows her off while getting acquainted with Julie under false pretenses. What a mess. Can “Southwest General” recast Dorothy to Michael?
9. “Sideways” (2004) – Miles (Paul Giamatti) plans a chill bachelor party trip for his best buddy, Jack (Thomas Haden Church), and with zero hijinks or foolishness planned. Just a short drive up the Southern California coast to wine country, where they will drink, eat, and then play plenty of relaxing golf, but not necessarily in that order. Jack has different ideas, like hooking up with a beautiful winery barista named Stephanie (Sandra Oh). Stephanie and Jack have a torrid good time, but he fails to mention that he’s getting married…to her pronounced surprise. “You’re getting married on Saturday???” Ouch.
8. “West Side Story” (1961, 2021) – Okay, generally speaking, Maria (Natalia Wood, Rachel Zegler) and Tony’s (Richard Beymer, Ansel Elgort) initial love affair doesn’t make them a bad couple at all. These two young people love one another and offer mutual respect, but once Tony kills Maria’s brother Bernardo (George Chakiris, David Alvarez), that should’ve ended this romance faster than you can say, “You killed my brother? Goodbye.”
7. “Bridesmaids” (2011) – Kristen Wiig and Annie Mumolo wrote one of the funniest comedies of the 2010s in “Bridesmaids”, the story of a down-on-her-luck and unlucky-in-love 30-something, Annie (Kristen Wiig). Annie falls into countless, hilarious scenarios during the lead-up to her BFF’s wedding – where Lillian (Maya Rudolph) asked her to be the maid of honor – but also within her fragmented daily life, where she lives with a weird brother and sister and dates a total jerk. Dating is a loose term, as Ted (Jon Hamm) and Annie occasionally sleep together. He calls her his “f*** buddy” without a second thought, and when Annie asks him to attend Lillian’s wedding, he responds, “No, I don’t want you to have to explain to all of those people what our relationship is, you know. That would suck for you.” Well, he has a point.
6. “Up in the Air” (2009) – Jason Reitman’s best film features one of George Clooney’s very best performances, as he plays Ryan Bingham, a bachelor, who spends his days flying around the country and letting people go. Not romantically, he’s a consultant who walks into office buildings, faces workers – who he’s never met – and lays them off. It’s a soulless existence, but he looks forward to earning 1,000,000 airline miles and regularly connecting with Alex (Vera Farmiga). Ryan and Alex have an occasional love affair while they’re on the road, but when he thinks they could be something more, she gives him a sudden and cold reality check in one of the most heartbreaking moments in 21st-century cinema.
5. “Sixteen Candles” (1984) – This John Hughes high school comedy may be his best, although some areas haven’t aged particularly well. Regardless, Samantha (Molly Ringwald) is beside herself because everyone in her family forgot her 16th birthday. The horror! She’s feeling the whole teenage awkwardness thing without her parents, grandparents, and siblings having a collective case of amnesia, and she pines for Jake Ryan (Michael Schoeffling), the most popular boy in school. He’s dating Caroline (Haviland Morris), a blonde bombshell and the most beautiful girl on campus, but their seemingly solid relationship seems to be standing on a foundation of jello. Caroline invites the entire planet to his parents’ house for a party, and Jake convinces her – while she’s drunk – that someone else – a freshman geek, Ted (Anthony Michael Hall), is him. Of course, she sleeps with Ted, off-camera. See, this movie doesn’t age well in spots.
4. “All About Eve” (1950) – No, Margo Channing (Bette Davis) and Eve Harrington’s (Anne Baxter) relationship isn’t romantic, but it’s one of the most toxic working ones in cinema history. Margo is a big-time Broadway star who rides success like surfer Robert Kelly Slater shoots the curls. However, she’s just turned 40 and is concerned about her career. When she meets Eve, a soft-spoken, up-and-coming actress, Margo doesn’t give her a second thought. Oh, that’s a mistake, because Eve has career plans of her own…namely HER name on the marquee!
3. “Play Misty for Me” (1971) – Sixteen years before Glenn Close terrified millions and millions of men in “Fatal Attraction” (1987), Jessica Walter earned a Golden Globe nomination in Clint Eastwood’s directorial debut by causing nightmares for probably the same number of guys in 1971. In the coastal town of Carmel, Calif., Dave (Eastwood), a disc jockey, has a fling with Evelyn (Walter), his number one fan. Their next few encounters, however, morph into awkward confrontations, as she insists on a commitment while waving neon-flashing billboards that spell KOOKY, UNSTABLE and DANGEROUS. Poor Dave. Well, it’s not like he doesn’t see the madness coming. We certainly do!
2. “Casino” (1995) – Sam Rothstein (Robert De Niro) loves the casino business, and he pours his blood, sweat, and tears into Las Vegas’ Tangiers. Well, not exactly. He spills sweat into the gambling outfit, but his friend Nicky Santoro (Joe Pesci) splatters blood as the mob’s ruthless heavy. Unfortunately, Sam drops figurative tears over his brutally unreasonable wife, Ginger (Sharon Stone). Ginger, a gorgeous former prostitute, has her photo in the dictionary under the phrase more trouble than she’s worth. In addition to abusing drugs and alcohol, she kidnaps their daughter, cheats on Sam with Nicky, and in the process, asks him to kill her husband. No, Sam is no picnic, but any man living in an abusive relationship will have marriage PTSD watching Martin Scorsese’s movie.
1. “Leaving Las Vegas” (1995) – Nicolas Cage won an Oscar in this heartbreaker of a film, where a Hollywood screenwriter, Ben Sanderson (Cage), loses his job and family, so he moves to Las Vegas to drink himself to death. Ben’s story would be lonely, but he meets Sera (Elizabeth Shue). She’s a prostitute, and he moves into Sera’s place, under two conditions: she doesn’t question his drinking, and he doesn’t disapprove of her profession. Naturally, mutual adoration clouds their initially-met requirements, as these two lonely, broken people try to make an impossible thing work. This is a tough but unforgettable watch.