The Top 25 Men Who Look Like Old Lesbians

By Keith Mays January 6, 2008 903,060 views

Take a man. Add eye work (unisex glasses if eye wear is needed)and Botox. Mix in a bad haircut or unfashionably long hair--if possible a dye job. A little doughy-ness doesn't hurt, either. Have a weakness for turtlenecks and by all means fight aging like it's a battle you can win if you try just a little harder, and there you have it: The winning formula to become a man who looks like an old lesbian.

We asked Keith Mays, author of the blog that started a phenomenon and pioneer in the field of men who look like old lesbians, to run down the 25 best examples of this confounding phenomenon and he happily obliged, including a handful of newly discovered men who look like old lesbians.

#25.

Chuck Klosterman

He Is:

A Pop-culture obsessed and farm-raised hipster who writes for GQ and ESPN.

Looks Like:

Someone who has penned 14 books on the spiritual nature of the vulva.

#24.

Al Franken

He Is:

Writer. Possible candidate. Rush Limbaugh tormentor.

Looks Like:

The art director of Lands' End catalog.

#23.

Jon Bon Jovi and Richie Sambora

They Are:

Founding members of Bon Jovi.

They Look Like:

They found a career resurgence as Le Tigre.

#22.

Robert Redford

He Is:

Actor. Director.

Looks Like:

The head of Women's Studies at Community College of Denver.

#21.

Don Imus

He Is:

The Disc jockey and humorist whose comments about the Rutgers University women's basketball team in 2007 led to the name "Imus" being mentioned on a college campus for the first time in 35 years.

Looks Like:

Someone who has lived with the same woman of color she met while working at San Mateo Y in 1962.

#20.

Warren Beatty

He Is:

Actor. Director. Former BFF of Carly Simon.

Looks Like:

The famed foe of Bobby Riggs.

#19.

Roger Ebert

He Is:

Pulitzer prize-winning columnist and film critic. Screenwriter whose films include Beyond the Valley of the Dolls.

Looks Like:

A late 1950s feminist who currently designs non-gender specific lingerie and underwear.

#18.

Kyle MacLachlan

He Is:

Actor known for his work with David Lynch and Elizabeth Berkley.

Looks Like:

A manager of a website about two pet dogs.

#17.

Masi Oka

He is:

Actor. Time Magazine whiz kid. Reported I.Q. of 180 (same as cast of Carpoolers).

Looks Like:

An author of a paper stating sex with a man is, by definition, a hate crime.

#16.

Mo Rocca

He Is:

We're not really sure what he actually does.

Looks Like:

A time-traveling lesbian from the future.

#15.

John Denver

He Was:

Singer. Country boy. Aviator.

Looks Like:

The founder of Colorado's first Lesbian Games, a non-competitive Olympics guaranteeing "participation trophies" for all entrants.

#14.

Peter Criss

He Is:

Musician. Drummer in bottom-feeding glam rock group.

Looks Like:

A collector of cat memorabilia.

#13.

Lance Burton

He Is:

Creepy Las Vegas-based magician.

Looks Like:

A K.D. Lang stand in.

#12.

Gary LeVox

He Is:

Lead singer of Rascal Flatts.

Looks Like:

A stage security at the Lilith Fair.

#11.

Richard Butler

He Is:

The Molly-Ringwald-serenading lead singer of the Psychedelic Furs.

Looks Like:

The co-founder of online erotic products store exclusively for lesbians, "Toys for Twats."

#10.

Dana Carvey

He Is:

Comic. Actor. Drummer. Impersonator of the President Bush with more successful foreign policy. In 1990s, he partnered with fellow SNL alum and man who looks like an old (or middle-aged) lesbian, Mike Myers, in a series of successful films about life in the suburbs.

Looks Like:

The runner of a rescue service for emotionally abused cats.

#9.

Rick James

He Was:

Musician. Famously sampled funk legend. Freak with supposed super abilities. Fan of hair extensions. Troubled individual.

Looks Like:

A person who reportedly married lesbian comic who goes by the single name "Margaret."

#8.

Simon Le Bon and other members of Duran Duran

They Are:

Musicians. Video stars. Inventors of the 1980s. Minstrels for Princess Diana.

They Look Like:

Financiers of such lesbian-themed films as The Secret That is My Garden and Rocky V.

#7.

Tim Robbins

He Is:

Actor. Writer. Tall person. Compulsive do-gooder in a less crazy than Sean Penn way.

Looks Like:

Winner of 12 straight division wins as coach of Florida Gators women's volleyball team in the late 1970s and early 80s.

#6.

Mike Nichols

He Is:

Writer. Director. Comic. Long-time partner to morning news show anchor Diane Sawyer. Directed Angels in America and Catch-22.

Looks Like:

Director of four episodes of The L Word.

#5.

Morten Anderson

He Is:

Football player. Ageless place kicker.

Looks Like:

A guard in women's prison.

#4.

Mike Myers

He Is:

Comic actor. Writer. Scatalogical-minded, sequel-happy entertainer at both Scottish and English accents who, in past films, has pointed out shortcomings in U.K.'s dental hygiene.

Looks Like:

An activist, promoting causes of transgender animated characters and company logos.

#3.

Ricky Gervais

He Is:

Comic. Writer. Actor. Creator of the hugely popular The Office and the somewhat less popular Extras.

Looks Like:

Someone who moved to Aleutian Islands with social worker partner and is studying to be a priest in the Anglican Church.

#2.

Kim Jong-il

He Is:

Leader of North Korea.

Looks Like:

A Lea-DeLaria-impersonating soccer mom.

#1.

Bruce Jenner

He Is:

An old lesbian.

Looks Like:

An old lesbian.

In some cases, it has to be just the right photo ...

... In other cases, it is, I admit, a little unfair ... the result of an unfortunate hairstyle or fashion of a certain era ...

... other times, it may be that it's a conscious effort by the person to look androgynous or just plain weird ...

... or it could even be a role the person is playing that I'm unaware of ...

... then there's Bruce Jenner. In photo after photo, pose after pose

... with family ... in a role ... giving a speech ... dressed for a night out at My Sister's Room in Atlanta ... he never fails to deliver ...

Bruce Jenner. A man who truly looks like an old lesbian.

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380 Comments

This creeped me out to no end. I happen to have a mother who's well into her fifties and a lesbian. She has a partner who's in her late forties (and obviously a lesbian as well). These guys look *so* much like the both of them. *shudders*

10/26/2009 11:37:53 PM

Enamaris

I disagree on Franken, Masi Oka and Tim Robbins. Also, Rick James, the Bon Jovi guys and Robert Redford look like they were caught on bad days. Spot on with Klosterman and Ebert (Though I respect those two), MacLahclan, Butler and Bruce Jenner. Mike Myers I'm not so sure of.

10/26/2009 9:10:06 AM

Ifrit

i like how all it really takes to look like an old lesbian is an androgynous hair cut and a pair of glasses.

9/27/2009 7:51:47 PM

hilah

Aw! not Morton Andersen!! He's the Saint's all time leading scorer!! What about Al Gore? Hillary Clinton...wait...

8/5/2009 1:05:47 PM

Brixy

The Robert Redford one just killed me. Thanks!

7/21/2009 12:10:54 PM

scriber7

My only problem with this list is that Chuck Klosterman is NOT a hipster. He doesn't like 80s music and pop culture because it's "retro" or "ironic" or whatever. He actually grew up in the 80s; he likes cheesy hair metal because he genuinely thinks it's good.

Yes, I'm a huge fan of his and I might sound really biased but trust me, if you read the book "Fargo Rock City" by him you can tell that he is no hipster.

...He does look like an old lesbian, though.

7/9/2009 4:40:35 PM

Slopez

No bruce vilanch? fail

7/4/2009 11:38:20 AM

dogcow

Clay Aiken needs to go up there. He is the clone of Billy Jean King (A true old lesbian)

6/29/2009 4:45:38 PM

smokedhog

you missed one: where is Steve Tyler?! giggled all the way through it anyway!!

6/17/2009 10:22:17 AM

sportster

I don't know...I suppose your mileage may vary, but Masi Oka looks more like a rather cute, thirtysomething lesbian to me. :D

5/27/2009 11:54:37 PM

Farseer-Lolotea

how is zac efron not on this list?!

5/12/2009 9:23:31 PM

snowfan

number 10 is the BEST!

3/24/2009 7:19:27 AM

milestarcar1994

Boy what a coinkidink!!
My Wife's Great Uncle and
his Daughter came to visit us
Saturday.
Anyway,her Cousin is Gay and she brought her'Life Partner'with her!!

3/1/2009 5:06:07 PM

TheEnemyBelow

Don't forget about Alec Baldwin!!
Since KIm Basinger left him,he looks like he's just lost his'femme'life partner!!

2/13/2009 4:57:37 PM

TheEnemyBelow

What about Bill Parcels? Looks like: junior high school girls' gym teacher.

2/4/2009 4:02:10 PM

brightonrock

How about Batiuk and Ayers creators of "Crankshaft"

1/29/2009 11:01:27 AM

Fingers

Man whats with the Alaska quips? Back off