--- description: Find out why "I Could Never Be Your Woman" is on TIME's list of the 50 most underappreciated movies of the 21st Century. title: 'I Could Never Be Your Woman' Is on The 50 Most Underappreciated Movies of the 21st Century image: https://static.time.com/v3/assets/bltea6093859af6183b/blt5eed08bd41435d8d/6998cbd783ec37574fc7b265/Underappreciated-Movies-I-Could-Never-Be-Your-Woman.jpg?branch=production&width=3840&quality=75&auto=webp&crop=16:9 --- Feb 04, 2026 # _I Could Never Be Your Woman_ Amy Heckerling by [Stephanie Zacharek](/author/stephanie-zacharek/) ## Stephanie Zacharek Update your preferences in [Account Settings](/account/preferences/) Close Film Critic  Paul Rudd and Michelle Pfeiffer in "I Could Never Be Your Woman", 2007 Paul Rudd and Michelle Pfeiffer in "I Could Never Be Your Woman", 2007Weinstein Company / Everett Collection Writer-director Amy Heckerling’s [_I Could Never Be Your Woman_](https://time.com/7302138/clueless-anniversary-amy-heckerling-career-appreciation/ "undefined") could be the greatest early-2000s romantic comedy you’ve never seen. It’s also one of the great romantic comedies of its era, period. If you were of moviegoing age at the time of its release, you may be wondering how you missed a picture starring Michelle Pfeiffer as a 45-year-old divorced mom and TV sitcom producer who falls for a much younger actor, played by Paul Rudd. (This is also a movie that features Tracey Ullman playing Mother Nature, and it was the feature debut of a young Saoirse Ronan.) The reason _I Could Never Be Your Woman_ may have eluded you? A botched theatrical-release deal that had nothing to do with Heckerling (best known for _Clueless_) or the quality of the movie. (It was released in certain European markets in 2007 and in the States, it went straight to DVD in 2008.) This is an unapologetically delightful picture, one that’s fully in tune with the stresses and joys of the December-May romance. How often, even a quarter of the way into the 21st century, do we see believable pairings of older women and younger men onscreen? It’s no surprise that Heckerling, one of the most gifted comedic writer-directors of her era, was thinking about it nearly two decades ago. 'I Could Never Be Your Woman': 50 Most Underappreciated Movies ```json [{"@context":"https://schema.org","@type":"Article","@id":"https://time.com/collections/50-most-underappreciated-movies/7353514/i-could-never-be-your-woman/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/collections/50-most-underappreciated-movies/7353514/i-could-never-be-your-woman/"},"headline":"I Could Never Be Your Woman","datePublished":"2026-02-04T12:52:28.000Z","dateModified":"2026-03-03T01:04:41.713Z","description":"","url":"https://time.com/collections/50-most-underappreciated-movies/7353514/i-could-never-be-your-woman/","keywords":["movies"],"thumbnailUrl":"https://static.time.com/v3/assets/bltea6093859af6183b/blt5eed08bd41435d8d/6998cbd783ec37574fc7b265/Underappreciated-Movies-I-Could-Never-Be-Your-Woman.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","author":[{"@type":"Person","name":"Stephanie Zacharek","jobTitle":"Film Critic","url":"https://time.com/author/stephanie-zacharek/"}],"creator":"Stephanie Zacharek","articleSection":"Entertainment","image":[{"@type":"ImageObject","url":"https://static.time.com/v3/assets/bltea6093859af6183b/blt5eed08bd41435d8d/6998cbd783ec37574fc7b265/Underappreciated-Movies-I-Could-Never-Be-Your-Woman.jpg?branch=production&width=1200&quality=75&auto=webp&crop=1200:675&height=675","width":1200,"height":675}],"publisher":{"@type":"Organization","name":"Time","url":"https://time.com/","logo":{"@type":"ImageObject","url":"https://time.com/images/logo.png","width":528,"height":156},"foundingDate":"March 3, 1923","sameAs":["https://www.facebook.com/time","https://www.instagram.com/time/?hl=en","https://twitter.com/time","https://www.pinterest.com/timemagazine"]}},{"@context":"https://schema.org","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"/section/entertainment/","name":"Entertainment"}},{"@type":"ListItem","position":2,"item":{"@id":"/tag/movies/","name":"movies"}},{"@type":"ListItem","position":3,"item":{"@id":"https://time.com/collections/50-most-underappreciated-movies/7353514/i-could-never-be-your-woman/","name":"I Could Never Be Your Woman"}}]}] ```