Jennifer Coolidge is a testament to what great talent, confidence, charisma, and wit can bring to the table in Hollywood. The entertainment industry has a long, tired history of misogyny and mistreatment of women, particularly older actresses, but Coolidge has defied the odds by continuing to shine into her 50s and 60s. Coolidge’s immense comedic skills have broken the mold for decades now.
Jennifer Coolidge’s most famous role is arguably her iconic portrayal of Stifler’s Mom in the cult classic American Pie films. Twenty years later, she received well-earned awards publicity with an Emmy win for ditzy dame Tanya McQuoid on HBO’s hit The White Lotus. Audiences will get to enjoy her presence in the second season of the show premiering on October 30, so we thought this would be a great time to celebrate the greatest roles of her career!
Karen Calhoun – The Watcher
Call it recency bias, but how could we not include Coolidge’s most recent role? The Watcher has been the perfect mysterious binge during spooky season, and Coolidge’s character relieves tension and forces us to laugh at the absurdity of her remarks. She plays the realtor who sells the home at 657 Boulevard, adding levity to situations that otherwise would not have any. This is also a solid summation of the type of stuff Coolidge usually does on the movies and shows she appears in.
Aunt Fanny – Robots
Jennifer Coolidge has one of the most unique voices in Hollywood. One second she can sound crazy, another second she makes us believe her character is clueless all by the tone of her delivery. This makes her a talented voice actor, and her appearance in Robots in 2006 as a machine with a big booty is hilariously fitting. Only Coolidge could make a robot sound innocently sexual enough for the movie to still be rated PG. And yes: this character’s name was changed for the U.K. release.
Paulette Bonafonté – Legally Blonde
The Legally Blonde series of films is known for Elle Woods’ (Reese Witherspoon) winsome takedown of female stereotypes as she transforms into a brilliant law student in college. Much like any comedy film, the meat of the entertainment comes from the quirks of the side characters, and Jennifer Coolidge’s interpretation of Elle’s friend, Paulette, is very endearing. She plays off Witherspoon very well in a myriad of scenes in the nail salon, gossipping and attempting to give advice to Elle with her signature naivete.
Sophie Kachinsky – Two Broke Girls
A show that never saw a sexual joke or an distasteful comment it didn’t like, Two Broke Girls was a moderately successful female buddy sitcom that ran on CBS right as the multi-camera sitcom started to fade in the 2010s. The concept of the show was nothing novel, but Jennifer Coolidge’s take as the girls’ Polish immigrant neighbor never fails to deliver the laughs. It’s not easy to fire off witty line after witty line with a fake accent, but Coolidge leans into all of the corny aspects of Sophie Kachinsky, stealing every scene she appears on the TV.
Fiona Montgomery – A Cinderella Story
If you’ve ever seen a .gif from a Jennifer Coolidge character online it’s likely from 2004’s endlessly quotable A Cinderella Story, in which she plays the evil stepmother Fiona Montgomery. Finding an actor who can torment a young Hillary Duff while still maintaining an air of likability can’t have been easy. But Coolidge is able to pull off the impossible and become a modern Cinderella villain.
Sherri Ann Cabot – Best in Show
Of the six mockumentary films directed by Christopher Guest, Jennifer Coolidge has been in four (missing only Waiting for Guffman and Family Tree). The actress is great in all of them but her best mockumentary role is definitely her first: Sherri Ann Cabot in 2000’s Best in Show. Cabot is an Anna Nicole Smith type married to a very old and very rich man. While she claims to love her husband and have a lot in common with him, she’s also clearly carrying on an affair with the family dog trainer Christy Cummings (Jane Lynch). Coolidge is always great enough on her own but pairing her with the equally talented Lynch makes Best in Show a truly hilarious experience.
Jeanine Stifler – American Pie
As far as coming-of-age films go, American Pie was quick to take the training wheels off its characters. It’s the type of teenage movie that parents weren’t comfortable with their adolescents watching, and for good reason. Sex, sex, and more sex was the name of the game for this early-aughts comedy, and Jennifer Coolidge certainly added to the sensual energy on the screen with her iconic portrayal of Stifler’s mother. Her turn as the MILF who all the teens dreamed of was a role completely suited to her magnetism.
What’s your favorite role in Jennifer Coolidge’s career? Let us know in the comment section!