Drew Barrymore has been a fixture in Hollywood since she was a little girl, so I figured it’s high time we take a look at her historical film roles. There’s not much, but some of my favorite flicks of all time are on this list.
Bad Girls (1994)
The early ’90s saw an explosion of hip, edgy Westerns blowing up the big screen and I guess someone somewhere thought, “What the world needs is Tombstone, but with sexy ladies.” The result was this iconic kitsch-fest, and I’m not mad about it.
Ever After (1998)
My absolute favorite movie of pretty much ever, and y’all can fight me on it if you disagree. This retelling of Cinderella hits me in all the right ways, including the costuming.
Riding in Cars with Boys (2001)
Set over the course of about a decade starting in the mid ’60s, this is an underrated film that shows Drew in her prime.

Confessions of a Dangerous Mind (2002)
Drew plays the wife of Chuck Barris (played by Sam Rockwell) in this dizzying reality-bending biopic about the host of “The Gong Show.”
Grey Gardens (2009)
Does it get any more iconic than Little Edie? Drew plays Little Edie Beale in this biopic about two eccentric women living in a decaying Long Island mansion.
What’s your favorite Drew Barrymore historical role? Share it with us in the comments!







No contest! Ever After!
Seconded. I love a well-costumed feminist fairy tale.
I won’t fight you on Ever After, which is my personal favorite costumed Cinderella retelling, followed by the genius of Sandy Powell’s for the Disney remake!
An idea for a post: Top Five Favorite Costumed Cinderella retellings?
Are there enough with a historical costume angle? Ever After (Italian Ren), The Slipper and the Rose (18th-c) … the one Sandy Powell costumed was maybe 1950s but mostly just fantasy. IDK, but I’m also nose-deep in Snark Week so can’t research it ;)
There’s a couple historically inspired costumes in the 2021 Cinderella flick by Ellen Mirojnick, or the 1997 version of R&H’s Cinderella, not to Mention the 17th century inspired costumes for an adaptation of Gregory Maguire’s take on Cinderella.
With the exception of the movie about Chuck Barris, I’ve seen all of these.
I love Ever After. It’s like a hug for my brain. And I looooove Danielle’s costume ball gown. If I had skills or money I’d have a replica.
I love Drew Barrymore in everything, but I have to say my favorite role of hers was in Charlie’s Angels (yes, i know not a Frock Flick). :)
Wedding Singer – I know – too recent era. XD
Hehe appropriate username.
I love the Wedding Singer. One of my absolutely favorite movies of all time (and soundtracks). If this website continues another decade or two maybe Trystan will let us cover flicks post-1969. 😂
I’m a HUGE Wedding Singer fan, duh, I’m an ’80s girl! But that’s just way too recent. We need some standards around here ;)
Every single one an absolute blinder. She is iconic.
Just wanted to say, I watched Grey Gardens following your post last year, several years after having seen the original Grey Gardens. So glad I did. It offered a lot of background that the original didn’t, and I thought Drew Barrymore was fabulous in it.
GLARES AT ‘BAD GIRLS’ –
You mean ‘Tombstone, but focussing on sexy ladies’, because please allow me to assure you, TOMBSTONE has eye candy to burn.
On a less serious note, I always wonder if Drew Barrymore is more disappointed or more relieved at the thought of the long career in Frock Flicks her Old World beautiful face might have condemned her to had she not been born All-American.