The 50 Funniest Women of the Past 50 Years: #20-11

Make people laugh and they won't even realize you're making them think. Over the past 50 years, women have broken through the glass ceiling time after time, shattering stereotypes and thumbing their noses at the old chestnut that “Women aren't funny.” Fact: Anybody who says women aren't funny doesn't want them to be funny.

We're looking back on the 50 funniest women of the past 50 years, their contributions to comedy, and their enduring legacies that inspire men and women alike. These are the 50 women who have helped (and are helping) to introduce the next class of hilarious women, which will inevitably include Amy Schumer, Lena Dunham, Mindy Kaling, Tig Notaro, Chelsea Handler, Maria Bamford, Aubrey Plaza, and Kate McKinnon.

Keep in mind this list only includes women who are primarily performers in movies, television, and standup comedy. That's why you don't see legends like Nora Ephron, Anne Beatts, and Elaine May here. Also note that this list chronicles the last 50 years; women who dominated prior to 1965 like Lucille Ball, Moms Mabley, and Elizabeth Montgomery miss the cut for that reason. We'll be counting down 10 new women every day this week.  

Come back tomorrow for #10-1. Today we've got #20-11.

(Catch up with #50-41, #40-31, and #30-21.)

20. Margaret Cho

It is nearly impossible to think of a touchy topic that Margaret Cho hasn't addressed and deconstructed with unceasing attitude since she became a standup superstar in the early '90s. As the first Asian-American woman to front a network sitcom, Cho has been a pioneer who is not afraid to get as angry or as bleak or as vulnerable as a joke requires.

Funniest moment: Her impersonation of her mother? Is an eternal treat.

19. Kristen Wiig

For decades, the dudes of “Saturday Night Live” have parlayed their tenure into lasting careers of gauche, gross-out comedy movies. But Kristen Wiig proved the ladies can be just as hilariously crass as anyone, if given half a chance. From her dead-on impersonations on “SNL” to her meteoric rise as one of the funniest women in the business, Wiig is busting glass ceilings to open the floodgates for flawed, funny, female characters.

Funniest Moment: Any of her impersonations, but I'm always partial to her take on Cinderella.

18. Wanda Sykes

Thank goodness her NSA job was boring, or Wanda Sykes might never have stepped onto the Coors Light Super Talent Showcase stage in 1987. And that would've been a tragedy for comedy. Never one to mince words, Sykes has made a successful career of making intelligent criticism of political and sociological touchstones. A champion of equality, Sykes uses her high profile to shine a light on causes such as supporting marriage equality.

Funniest Moment: Proving that no subject is taboo as long as you don't make fun of the victims, this bit by Sykes is held up as a perfect example. (NSFW language)

17. Lisa Kudrow

Lisa Kudrow bounced around under the radar for years. Childhood friends with Jon Lovitz, she cut her teeth performing in comedy troupes while trying to break into television. Her overnight success – like most – was anything but. However, she catapulted to fame and became a household name with the success of “Friends.” Her hippie character of Phoebe is one of the most instantly recognized icons of the 90s.

Funniest Moment: This collection of some of Phoebe's best moments only scratches the surface.

16. Amy Poehler

A veteran of Second City and a founding member of the Upright Citizens Brigade, Poehler has always had a knack for delivering a wicked punchline with a Cheshire grin. As one of the premiere cast members on “SNL” in the early-to-mid '00s she brought her sunny cynicism and character-building chops to bear on a number of memorable recurring characters including obnoxious one-legged reality-show contestant Amber (“Yeah, I farted. Jealous?”), hyperactive pre-teen Kaitlin and scrappy 90-pound parking valet Jojo, and with Tina Fey she broke ground as co-anchor of the first female “Weekend Update” team. Her ensemble spirit has been put to winning use on “Parks and Recreation,” and she and Fey have set a new bar for awards-show hosts as co-emcees at the Golden Globes two years running. FIlm-wise, her performance as obnoxious surrogate mother Angie in “Baby Mama” is an underrated comic gem.

Funniest moment: I'll forever love her as Regina's tracksuit-wearing “cool mom” in “Mean Girls.”

15. Julia Louis-Dreyfus

An 18-time Emmy nominee, Julia Louis-Dreyfus is the reigning queen of television sitcoms. She began as a breakout talent on “SNL” in the '80s but became a legend by thrilling us with her horrible dancing and worse friendship skills as Elaine Benes on “Seinfeld.” “The New Adventures of Old Christine” proved she could rule her own sitcom (and win an Emmy for it), and now she's serving up unsmiling, grimly profane laughs as Selina Meyer on “Veep.” Julia Louis-Dreyfus is an unswervingly focused and hilarious actress, and she may be — I'll say it — the most beloved performer on TV today. Her power is unspeakable.

Funniest moment: This vulgar perfection on “Veep”

14. Kathy Griffin

Though I'm sure Kathy Griffin appreciates being called hilarious and provocative, she is perhaps most proud of being endlessly hard-working. The “D-List” doyenne has graduated from soubrette sitcom roles to comfortable status as a Carnegie Hall marquee superstar, and she fought her entire way to the top. Though she's known for calling out celebrities for their bizarre behavior, Griffin's act is about justice and intelligence. She'd rather stand up for common sense than watch as misogyny, idiocy, or (perhaps most pressingly) self-seriousness dominates pop culture. Her improvisational flair aids her in telling fantastic anecdotes, and as we march on without Joan Rivers here to help crucify mundane celebrities, we need Kathy Griffin's rebellious streak to propel us through another generation of Hollywood insanity.

Funniest moment: Her nearly two dozen standup specials are all great, but let's take a moment to remember that time she told Jesus to suck it.

13. Tracey Ullman

It doesn't seem like a coincidence that Tracey Ullman embodied so many different characters on “Tracey Takes On,” her Emmy-winning HBO sketch series, because Ullman herself has had so many different personae since we first learned of her wacky talents on “The Tracey Ullman Show” in the '80s. The onetime pop singer began as a “traditional” variety star in the vein of Carol Burnett and has evolved through the years into a spikier, more provocative act on her fabulous “State of the Union” series. Ullman's seemingly limitless ability to impersonate others and command attention with a host of other talents is second to none. She is un-self-consciously able to do anything, and that is both shocking and fabulous.

Funniest moment: This impersonation of Renee Zellweger as J.K. Rowling is scream-worthy.

12. Sarah Silverman

First things first, Sarah Silverman gave us my choice for the single greatest one-liner of all time: “When life gives you AIDS, make lemonAIDS.” But she's also a defiant provocateur whose droll and weird sense of humor belies steadfast conscientiousness. If “Jesus is Magic” didn't sell you on her wild righteousness, her fantastic “Sarah Silverman Program” and book “The Bedwetter” will do the trick. And best of all, she's f*cking Matt Damon.

Funniest moment: Here's a typically NSFW and hysterical bit about the Holocaust from “Jesus is Magic.”

11. Madeline Kahn

We could sit for hours trying to figure out the je ne sais quoi of Madeline Kahn, but it basically goes like this: She had a sincere charm dotted with moments of hilarious peculiarity. Her upper-crust veneer always seemed moments away from cracking and giving way to a panic attack or a few operatic screams. A favorite of Mel Brooks, Madeline Kahn could give you exasperated, vaudevillian loopiness (think “Blazing Saddles”), but she always paired it with a core of awkward vulnerability (think “Paper Moon”). And hell, she was awesome enough to improvise the “flames on the side of my face” monologue from “Clue.” She was superheroically talented, and there may never be another talent with as much silliness and soul.

Funniest moment: Impossible to pick, but after you re-watch her “Clue” appearance as Mrs. White 50 times, be sure to check out her amazing and profane monologue from “Paper Moon” a couple hundred more times.