This week, Maggie Gyllenhaal reminded us that ageism in Hollywood is alive and well – if you’re a woman, that is.  “There are things that are really disappointing about being an actress in Hollywood that surprise me all the time,” she told the Wrap. “I’m 37 and I was told recently I was too old to play the lover of a man who was 55. It was astonishing to me. It made me feel bad, and then it made me feel angry, and then it made me laugh.”  Related: Maggie Gyllenhaal: At 37 I was 'too old' for role opposite 55-year-old man  Some of us (hey guys) still haven’t made it to the laughter stage, especially since movies have a long and illustrious history of pairing older men with much, much younger female co-stars. In fact, it’s such a commonplace trope that to whittle a list down to 10 choices was daunting and almost impossible (almost). So to re-establish the ridiculous habits of Hollywood casting directors, here are 10 movies that deliver some seriously astonishing age gaps, and expect us to run with them. (So note: there’s no Lolita or American Beauty here.)  A terminally ill 28-year-old Winona Ryder (playing 22) falls for notorious playboy and 50-year-old Richard Gere (who plays 48) in 2000’s Autumn in New York, a Love Story-esque tale of a man being taught to love again via an early days Manic Pixie Dream Girl. The highlight? Vera Farmiga, who’s roughly Ryder’s age, plays his adult daughter.  While 2011 delivered Unknown, an action vehicle starring Liam Neeson (then 58), who tries to save his wife (January Jones, then 33), Third Person takes the cake with the pairing of Neeson (61) and Olivia Wilde (29), who plays his “lover” (terrible word), Anna. That’s a full January Jones-in-Unknown between them.  Truth: 1942’s tale of 41-year-old Humphrey Bogart reconciling his relationship with 27-year-old Ingrid Bergman is the stuff of classic cinema dreams. Is Casablanca a brilliant treasure? Of course. But it still doesn’t mean we shouldn’t acknowledge that the age difference exists, and should be indicative of that era, not our own.  Arguably, we could include a number of selections from Woody Allen’s filmography, but 2014’s Magic in the Moonlight takes the cake. With an age difference of 28 years between leads Emma Stone and Colin Firth, it’s one in a long line of Allen-curated young woman/older man dynamics. The next? 2015’s Irrational Man, starring Joaquin Phoenix and Emma Stone, with an age difference of 14 years. The twist? He plays her professor. (So at least the power imbalance will be complete.)  Edge of Tomorrow was an underrated movie that saw then 31-year-old Emily Blunt break out and take charge of an action narrative formerly reserved for her co-star, then 51-year-old Cruise. (The nickname “Full Metal Bitch” is truly the stuff of dreams.) In fact, for most of the film, it seemed the two would coexist as friends as opposed to romantic interests, but by the end, it seemed like Cruise’s character was more than willing to overlook that 20-year age gap.  Kind of like what he’ll be doing alongside 31-year-old Sarah Wright Olsen in the upcoming Mena.  Harrison Ford’s characters have a legacy of pursuing younger women (see: Star Wars, Working Girl, Blade Runner and Sabrina – though arguably, the last one isn’t his fault), but 1998 delivered the then 55-year-old actor paired alongside then 29-year-old Anne Heche. The clincher? Complete opposites, they’re stranded on a desert island. (So you can probably guess the rest.)  Johnny Depp’s characters are clearly going through something: in 1999, the 36-year-old was paired up with 19-year-old Christina Ricci in Sleepy Hollow. In 2006 (at 43) Depp romanced 21-year-old Keira Knightley in Pirates of the Caribbean: Dead Man’s Chest. And in 2011, he co-starred with 25-year-old Amber Heard, now his wife, in The Rum Diary. However, in 2012, 48-year-old Depp hooked up on screen with 24-year-old Bella Heathcote in Dark Shadows. And despite the Victorian era being a very different time, it just felt like more of the same old (and not old at all).  Let’s give Steve Carell and this 2012 black comedy credit: Seeking a Friend for the End of the World is less about falling in love à la Autumn in New York than it is about self-discovery. But casting directors still felt the need to pair the nearly 50-year-old Foxcatcher star with a then 27-year-old Keira Knightley who was great, but also more than 20 years younger than him.  Michael Douglas arguably attends the same school as Johnny Depp in that he has a long history of working with young co-stars. However, one-upping 1998’s Don’t Say A Word (in which he’s 20 years older than his on-screen wife, Famke Janssen) was 2001’s A Perfect Murder in which the veteran actor is married to Gwyneth Paltrow, who’s 28 years his junior. (Maybe we should write about that in Goop.)  Managing to win over waitress Helen Hunt with his personality (despite said personality being abrasive at best) and eventual grand gesture was Jack Nicholson in 1998’s Oscar-nominated As Good As It Gets. The two bantered well and had good chemistry (Hunt actually won an Academy Award for her role), but the age difference is still notable: 26 years exists between them, making this yet another example of “Why?”
Maggie Gyllenhaal said she was passed over for a role opposite a 55-year-old actor because she was too old – at 37. It’s part of a long, inglorious Hollywood tradition