In the new movie The Sessions, John Hawkes stars as a poet, paralyzed from the neck down due to polio, who hires a sex surrogate (Helen Hunt) to lose his virginity. Based on the real-life story of Mark O’Brien, the film debuted at this year’s Sundance Film Festival, where it won an Audience Award and a special jury prize for ensemble acting. Hawkes’ affecting performance won raves from critics, many of whom predict that the veteran character actor is a lock for a Best Actor nomination come Oscar season.

The Sessions, which opens October 19 in limited release, was also applauded for taking a sensitive, surprisingly light-hearted approach to its potentially difficult subject matter. Though the deep, ever-evolving relationship between Hawkes and Hunt (her character is married) might not be romantic per se, their unique situation got us thinking of some of the quirkiest and most unusual pairings in recent movie history. These films feature oddball couples who prove that love can grow even in the most unlikely of situations.

One reliable source of unlikely movie chemistry is the pairing of an uptight, repressed man with a free-spirited, spontaneous woman. Who can forget the surprisingly profitable business-romantic venture of a naive high school student and streetwise prostitute in Paul Brickman’s Risky Business? With the help of Lana (Rebecca De Mornay), the prostitute who initiates him into manhood, Joel Goodsen (Tom Cruise) transforms from a conventional, All-American “future enterpriser” to a cunning businessman when he turns his suburban house into a one-night-only brothel in this witty 1983 classic.

In Jonathan Demme’s Something Wild (1986), Jeff Daniels plays a similar kind of character 10 years down the line: An uptight yuppie who gets kidnapped by Lulu (Melanie Griffith), a wild, unpredictable woman who, in the span of a weekend, changes Charlie’s life and releases his inner free spirit.

Jim Carrey plays a meek, introverted man who embarks on a romantic journey with an uninhibited woman (Kate Winslet) in Michel Gondry’s Eternal Sunshine of the Spotless Mind (2004). Charlie Kaufman’s mind-bending script won a well-deserved Oscar and while the movie’s non-chronological pacing and science-fiction elements can get complicated, the main characters’ true-to-life romantic relationship keeps the movie grounded in reality.

The 1970s gave us some great quirky romantic couples. Perhaps the quintessential pairing is neurotic New Yorker Alvy Singer (Woody Allen ) and spacey Midwestern title character Annie Hall (Diane Keaton) in Allen’s Oscar-winning 1977 classic. Likewise, buttoned-up museum curator Gena Rowlands and wacky hippie parking attendant Seymour Cassel find unexpected love in John Cassavetes‘ Minnie and Moskowitz (1971). Of course the king (and queen) of oddball pairings is Hal Ashby’s cult fave Harold and Maude (1971). It would probably be difficult to find a romantic pairing as polar opposite as Harold (Bud Cort), a young man obsessed with death, and Maude (Ruth Gordon), an old woman rejuvenated by the simple pleasures of living.

The notion of falling in love with a criminal is one that has been explored in a number of movies. In Buffalo ‘66 (1998), writer-director-actor Vincent Gallo plays Billy, a grungy ex-con just released from prison, who kidnaps Layla (Christina Ricci), a mild-mannered ballet dancer, so that he can lie to his delusional parents that they’re married. Despite the offbeat circumstances, Layla comes to realize Billy is emotionally damaged and, despite his problems, grows to love him.

In Steven Soderbergh’s Out of Sight (1998), a similar situation arises when a hardened federal marshal (Jennifer Lopez) finds herself falling for a suave bank robber (George Clooney) on the run. Named one of the 50 Sexiest Movies Ever by Entertainment Weekly, Out of Sight is an underrated crime-comedy-romantic-thriller that combines a multitude of genres. Yet at its core lies the white-hot romance between cop and criminal.

Gay romances have also proven to be a source for quirky pairings. In Kissing Jessica Stein (2001), a single, straight woman (Jennifer Westfeldt), successful in work but not in love, meets a gay woman (Heather Juergensen) through a personal ad and embarks on a hilarious, heartwarming journey into uncharted territory. The Birdcage (1996) centers around a mismatched pair of gay men (played by Robin Williams and Nathan Lane), with hilarious and touching results.

A different kind of love sparks in auteur Paul Thomas Anderson’s Punch-Drunk Love (2002), about a socially inept man (Adam Sandler) who becomes romantically involved with an odd, elusive woman (Emily Watson) who proves to be the answer to his lonely woes.

There are of course many more quirky pairings and oddball movie romances (so please leave your favorites in the comments section!), but what these movies prove is that love (whether romantic or otherwise) truly can conquer all, even in the most unexpected of scenarios.