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The 25 best romantic comedies to watch this Valentine's Day

5. Sleepless in Seattle (1993)

The romance: Widower Sam Baldwin (Tom Hanks) opens his heart after his wife's death live on radio, at the urging of his son Jonah. When Annie (Meg Ryan) hears his story, she re-evaluates her engagement and scribbles a letter to Sam asking him to meet her at the top of the Empire State Building... 

Why it wooed us: Nora Ephron's tale is now almost 30 years old, and had all the hallmarks of being a classic even then. It's funny and warm without drowning in schmaltz. Hanks and Ryan's palpable chemistry is a remarkable feat considering they barely share any screentime. 

4. Some Like it Hot (1959)

The romance: Jazz musicians Joe (Tony Curtis) and Jerry (Jack Lemmon) end up on the run after witnessing the St. Valentines Day massacre. Masquerading as buxom women, they hide out as members of touring all-female music troupe, Sweet Sue's Society Syncopators – where they meet Sugar Kane (Marilyn Monroe), a breathy singer who they each attempt to woo. In disguise... 

Why it wooed us: Billy Wilder pulled out all the stops at a time when censors frowned upon any kind of sexual tomfoolery. Shocking the MPAA with his tale of two transvestites after a bit of hot totty while escaping the clutches of the law, there's no finer environment for Curtis and Lemmons' comedic skills. 

3. Annie Hall (1977) 

The romance: Neurotic comedian Alvy Singer (Woody Allen) explores the doomed nature of his past romantic relationships, in particular his most recent paramour, Annie (Diane Keaton). The two meet through friends, and embark on what Alvy considers to be an unusual relationship. She's a free-spirited hipster while he remains the introspective analyst. 

Why it wooed us: The subtitled scene following the pairs initial meeting, on a Manhattan rooftop, is pure cinema gold: a sterling example of Allen's quick wit. While Annie and Alvy are conducting a seemingly trivial conversation concerning a date, subtitles flash up to reveal what's actually being conveyed. 

2. It Happened One Night (1934)

The romance: Snobby socialite Ellen Andrews (Claudette Colbert) goes on the lam, relinquishing her rights as heir to the family fortune to elope with her new spouse. On the way, she meets and falls for the charms of a no-nonsense journalist Peter Warne (Clark Gable) during a cross-country trip. 

Why it wooed us: The original rom-com, Frank Capra's flick is a landmark 'screwball' comedy. It introduced the now-popular formula of a mismatched couple who eventually fall in love. 

1. When Harry Met Sally (1989) 

The romance: Wise-crackin' Harry (Billy Crystal) and the progressive Sally (Meg Ryan) strike up a fiery friendship during a rideshare home from university, which ignites a series of chance meetings. Across a little more than a decade, the two challenge each other, bicker, disagree, yet continue to be drawn together.  

Why it wooed us: Based on the real-life tribulations of director Rob Reiner following his divorce, it was and still is a refreshing romantic comedy. The combo of Crystal and Ryan revived a gasping genre, exploiting the differences between the sexes to killer effect with heaps of guffaws that never seem contrived. And of course, there's Ryan's scene in the deli, making men (and women) the world over stand up and take notice. 

Gem Seddon
Gem is GR+'s west coast entertainment news reporter. She’s a bit obsessed with all things Aliens and Terminator.