50 Hottest Women Most Guys Fantasized About Growing Up

Becoming a sex symbol of legendary stature that defines a generation of women and men involves the planets and stars aligning at just the right moment in time. It requires a camera, canvass, or written prose to capture the spirit and charisma of a woman who represents everything we want, need, and desire. Occasionally those needs cross generations and even centuries of generations who will then fantasize about that character (real or not) until it becomes bigger than itself, such as in the iconic sex symbolism of Marilyn Monroe, Bettie Page, and even Cleopatra.

Every woman who has reached the status of a multigenerational sex icon started among the humble beginnings as a simple fantasy. Who did you fantasize about the most growing up? Do you think she has the potential to burn her legendary image into the fantasies of men for the coming generations to come? Well, we’re going to do our darndest to give her a boost in the right direction.

Marilyn Monroe

Not many women have an iconic photo that finds its way into the lockers and dorm rooms of seven generations of men with the same fantasy-inducing inspiration as the first. There is something special about the way the camera made love to Marilyn Monroe each time a single finger unveiled a roll of film to her presence. Whether her skirt was flying or she was swinging one leg out of a pool, she captured a young man’s imagination at a rate of about 5,000 words per second.

Monica Bellucci

Monica Bellucci

She became the oldest Bond girl to heat up the screen in 2015 when she appeared as Lucia Sciarra in Spectre. Monica was 50-years-old at the time. However, many of our readers may also recognize her as the face of many many Dolce & Gabbana advertisements back before the millennia. In 2001, she was the hottest cover model to land on Esquire’s February issue taking part in a rather appropriate topic about the Five senses. AskMen picked up on her in 2002, claiming her to be the most desirable woman at the time. And even if you were lagging a bit on your Men’s Mag subscriptions, by 2003 she was featured in both Maxim and Men’s Health, hitting the MH “100 Hottest Women of All-Time” falling in at number 21 (she was 38 at the time).

Danica McKellar (Winnie Cooper on Wonder Years)

Most teenage math-enthused girls know her as Danica McKellar the math teacher, but many of us guys remember her as Winnie Cooper from the television show, The Wonder Years. And if you ever ‘wondered’ about how real some of that awkward sexual tension between her and Kevin (Fred Savage) was, well, we can assure you that it was very real, both actors admitting that they shared their first kiss in life on screen right there before our eyes, and then went on to ‘crush’ on each other for the next couple of years. That was awful cute back in 1989… and if you were a budding teen at the time, it was also a bit sexy.

Jessica Alba

Jessica Alba

As we were watching Jessica’s new show, L.A.’s Finest, we were reminiscing about where it was that we first saw her. Perhaps it was from the 1994 comedy, Camp Nowhere, or maybe it was her recurring role on The Secret World of Alex Mack. But to be honest, we probably really took notice in the Fall of 2000 when a 19-year-old Alba played Max Guevera in the science-fiction series Dark Angel. We had some pretty worn out areas on our VHS copies of The Sleeping Dictionary (2003) and Sin City: A Dame to Kill For back in those days, but if you were too young to indulge in R-rated film, then all we have to say is Susan Storm of the Fantastic Four.

Scarlett Johansson

Scarlett Johansson

Scarlett may have been one of our earliest crushes, falling into the scene in 1994 at the tender age of nine in the film North, playing as the daughter of John Ritter. You may have also noticed her in films such as Home Alone 3 (1997, yeah, they actually made three of those), The Horse Whisperer (1998), Ghost World (2001), and Eight Legged Freaks (2002). By the time she was ready to become a full-fledged sex symbol, there was a slew of films waiting to justify this claim, including A Love Song For Bobby Long ((2004), He’s Just Not That Into You (2009), Don Jon (2013), Her (2013), and Under the Skin (2013).

Raquel Welch

Raquel Welch

There are many women on this list who have become a man’s greatest fantasy because of a film role that involved a bikini. However, Raquel Welch came at a time when the bikini was not so much a household everyday occurrence (we’re talking 1966, people). Many a boy in the 60s and 70s saw his first glimmer of a woman’s curves underneath a somewhat skimpy bikini masked to resemble an animal pelt of a cavewoman in the film, One Million Years B.C.. Welch claims that she has autographed millions of photos copied from this film’s publicity shots (at least one per day on average – she is now 81-years-old), so you do the math.

Cameron Diaz

Cameron Diaz The Mask

It was in 1990 that Cameron Diaz first landed a spot in her first teen magazine. At the time, she dreamed of becoming a zoologist and enlisting to travel Africa in the pursuit of learning more about lions. Instead, she was cast in the film, Mask (1994), opposite Jim Carey. She had little acting experience (She’s No Angel was her first video), but she took it all in stride along with some acting lessons and before she knew it she became Mary (Something About Mary) in 1998, a Charlie’s Angel in 2000, 2002, and 2003. She followed it up with many more blockbuster hits, and then in 2014, after filming, Sex Tape and Annie she gracefully walked off the set and has yet to return. All we can say is hold onto those childhood fantasies dearly.

Farrah Fawcett

While Farah’s sex symbolism was certainly catapulted by the television series Charlie’s Angels, it was this single swimsuit poster (above) that boosted her image to legendary status. There were 5 million copies sold back in 1976-1977, which quickly translated to over 12 million copies to this day. That has to be some kind of record we can assure you. She did not dawn a bikini as most of the women before her, because she preferred to cover up a childhood scar on her belly that she had always been a bit subconscious about. But it wasn’t the one-piece that had everyone talking, but rather the waves in Farrah’s hair that many men claimed spelled out the word, “Sex.”

Eva Mendes

We were trying to pinpoint the exact moment that Eva became a fantasy within our goto mental library, and we’d have to go with the year 2001 when she practically opened the film, Training Day, wearing just a tad more than her birthday suit. “For my art,” Eva has said. “I’ll do almost anything.” And then we saw her in a flawless white bikini in 2 Fast 2 Furious (2003), some black lingerie in Hitch (2005), and plenty of memorable magazine covers in between many other great films. But what is to come for the future generations now that Eva is a full-time mom and has kept herself well within PG-13 territory? We can only hope for a return to the Fast and Furious franchise, which has been tossed around the rumor mill a time or three.

Pamela Anderson

Pamela Anderson

Beyond those racy ads, a Playboy cover, high profile marriages, and of course, that “sex tape,” what most every man will remember most about Pamela Anderson is not her naked body, but rather that iconic red swimsuit. From 1992 to 1997, Pamela played C.J. Parker on the television hit, Baywatch. The show required either the knowledge of saving lives (one of the cast members was actually a lifeguard) or that you could wear a swimsuit and wear it well. “Baywatch is about – women in bathing suits,” David Hasselhoff once explained. “And what’s wrong with that?” Absolutely nothing, Mr. Hasselhoff.

Carrie Fisher

The gold metallic bikini became Carie Fisher’s calling card as a sex symbol for every sci-fi nerd and Barbarella Fan (we’ll get to her in a bit) back in 1983. That was the year that Star Wars: Return of the Jedi was released. What was going on in your mind while filming that scene, many fans have asked? To which Carrie would answer bluntly, “I couldn’t wait to kill him (Jabba the Hutt),” just so that she could get out of that outfit. Hey Carie, you did tell producers that you did not want anything “baggy or mannish” like your previous outfits from the first installment of Star Wars, so I guess you just can’t make everybody happy.

Megan Fox

Not a lot of guys will remember Megan’s supporting role in the TV sitcom, Hope & Faith. But you might be familiar with her bit bikini role in the 2003 blockbuster Bad Boys II (Megan was only 15-years-old at the time). No? Okay, then how about the 2007 megablockbuster Transformers, when Megan seductively bent over the hood of that rusty Chevrolet Camaro (Bumblebee) to admire his shiny set of headers?

Angelina Jolie

Angelina Jolie - Lara Croft - TombRaider

Before Jonny Lee Miller, Billy Bob Thornton, Brad Pitt, and all those babies, Angelina was a child star born through the loins of actor, Jon Voight, and actress, Marcheline Bertrand. She played the perfect ‘troubled girl’ that male audiences just could not help falling in love with again (Hackers 1995), and again (Gia 1998) and again (Girl Interupted 1999), and again (Lara Croft: Tomb Raider (2001).

Catherine Bach

When we mention seeing a pair of “Daisy Dukes” on the beach yesterday, many guys will know exactly what we’re talking about. But there is always at least one guy who has no idea what we’re talking about. For that one guy, Daisy Dukes is a character from the 70s-80s television show, The Dukes of Hazzard. She might as well have only had one outfit in her closet because all most guys can remember are those tight, cut-off jeans creeping into areas that have yet to be rated for this website.

Jessica Simpson

THE DUKES OF HAZZARD, (c) Warner Brothers

We have pondered this question for the last half hour: Is it possible for another actress to fill a pair of Daisey Dukes in the same wonderful way as the original? We don’t know, as we were too busy admiring Jessica Simpson in this hot pink bikini from the 2005 film variation of The Dukes of Hazzard.

Selena Gomez

Selena Gomez

Hardly any man is going to admit to falling for Salena as a toddler watching Barney and Friends (2002-2004), but that is likely where the spark fell into your crib and was blown and tended by Disney through such teenage hits as Hanna Montana, The Suite Life of Zack & Cody, and Wizards of Waverly Place. And then a bunch of photos and videos eventually emerged turning all those boyhood fantasies into reality. Well, maybe not your reality, but the reality that life and sex do exist outside of Disney and your imagination.

Sofia Vergara

Sofia Vergara

Sofia started a family at age 19, with both a husband and a newly born son. She was also en route to becoming a dentist when a gig hosting a television travel show and starring in a Spanish soap opera both fell into her lap. From there many guys admired her as an occasional fashion and swimsuit model, film character, beer spokesperson (Miller Lite), television host, and of course last but not least the television show, Modern Family.

Beyonce

Beyonce

You may not realize it but your infatuation with Beyonce Knowles-Carter may have started when she was just 12-years-old debuting on Star Search. But the fictitious character that you probably remember most is Sasha Fierce, the booty-shaking seductress she called upon for every stage performance she gave up until 2010 when she officially declared Miss Fierce dead. But as it turns out, the real Beyonce is just as talented and entertaining (maybe even more so).

Demi Moore

Here is a woman who that most men from any generation will have some ‘happy’ memory of from their youth, whether it was About Last Night (1986), Indecent Proposal (1993), Charlie’s Angels: Full Throttle (2003), or Blind (2017). Let us see, did we leave anything out? Oh, and you may have caught her in Strip Tease (1996) and probably wore out your VHS in several key scenes that shall forever be burned into our wildest fantasies.

Rihanna

There have been many great moments over Rihanna’s career for a man to fantasize about, but what seems to elicit the best from our imagination is her own patented flare for selfies.

Nicole Scherzinger

Nicole Scherzinger

When we heard a siren call our attention to the tune of “Don’t you wish your girlfriend was hot like me?” We said, I don’t know, hold on for a moment while we Google you. This was back in 2005, so the Internet was a little slow back then. And then Nicole and her gang of Pussycat Dolls appeared on our screen, confirming that we would indeed much rather have her as our girlfriend. And the fantasies just took on a life of their own from there.

Irina Shayk

Irina Shayk

Whether you’re a man of Sports Illustrated or Victoria’s Secret, you’ve probably admired the minimal coverings of model Irina Shayk a time or two. Or perhaps it was three or four, but who’s counting (well, I guess actually we are).

Miranda Kerr

2007 was a big year for both Meranda and us men, as she both became an official Victoria Secret Angel and was also featured in a cameo on the popular television show, How I Met Your Mother. From there, her clothing seemed to become more sparse as her popularity soared higher.

Christina Aguilera

Christina Aguilera

Talent can only get you so far, we’ve heard. And once you’ve hit that wall you can try stripping off your clothes and showing just enough skin to remain provocative. And this has worked quite well for Christina over the years, which has earned her a place of honor on our list.

Britney Spears

We are not sure what is more dangerous between the risky school girl outfit she wore in the video “Hit me, baby, one more time,” or the pink polka-dotted hotpants on the cover of Rolling Stone in 1999. And while our mom always told us that’s not the kind of attention a girl should want, it is the kind of hot mess that a boy’s/man’s best fantasies can grow from.

Cindy Crawford

Every generation has one woman that every woman either wanted to be, or every man wanted to have. For the ’90s, Cindy Crawford was just that woman, and this photo offers all the necessary explanations for such a bold statement.

Christie Brinkley

First, there was Christie’s Sports Illustrated Swimsuit Issues, and then her “red Ferrari girl” Cameo on National Lampoons Vacation (1983), which was followed up by her Playboy cover feature in 1984. And then 40 years later, Christie’s life went full circle as she once again graced the cover of Sports Illustrated for their 2014 edition. It is safe to say that no matter which generation you’re from, a bit of Christie Brinkley has jumpstarted your hottest fantasies in one way or another.

Claudia Schiffer

But what about Claudia Schiffer, you may be wondering. Yes, there was Claudia… and also Naomi Campbell, Christy Turlington, and Linda Evangelista. We could go on and on with 90’s supermodels, which is why we have to draw the line somewhere.

Karen McDougal

Karen McDougal

Before Trump and all the scandal, she was a cheerleader, and then a swimsuit contest winner (Michigan), Playboy Playmate of the Year (1998), and the first woman to ever appear on the Men’s Health cover in 1999.

Kaley Cuoco

Do you remember the time that Penny (The Big Bang Theory) sang “Soft Kitty” to Sheldon while he was sick in bed? Oh yeah, that was like the nerd version of Marilyn Monroe and “Happy Birthday Mr. President,” which is a high compliment to Kaley – a high compliment indeed.

Bo Derek

Bo

The movie was called 10 (1979), and it was a romantic comedy by Blake Edwards starring Dudley Moore and Julie Andrews. It was just that until Bo Darek ran across the beach in a ‘nude’ one-piece bathing suit. And then men began to play that scene back in their mind and noticed those sexy cornrows and sneakily pealed off that very thin layer of fabric, and boom… her legacy was sealed.

Denise Richards

WILD THINGS 1998

How many women’s legacies have been cast from a single bathing suit of epic proportions? Half of this list, but this time the swimsuit was ordered in an appropriate hue of “steel blue”. We just have two words for you: Wild Things (1998).

Jane Fonda

Barbarella (1968)

There have been many cult classic images that stick in your mind, but few as iconic as Jane Fonda in the film, Barbarella (1968). Have we seen it? Yes. Do we remember what it was about? No, but we do remember those skin-tight outfits. Oh yes, we do!

Aishwarya Rai

Aishwarya Rai

Okay, so you might not recognize the name, but she is ‘the dream’ of millions of men in India, and it’s easy to see why.

Catherine Zeta-Jones

When Catherine walked on the set of The Mask of Zorro in 1998 (she was 28 at the time), she considers that one of the pivotal moments when she realized that she had finally ‘made it,’ and well, we’d have to agree.

Heather Locklear (Jody Banks on The Fall Guy)

If you have ever watched any episodes of the 1980’s television classic, The Fall Guy, you can probably appreciate why Heather Locklear is on this list. If you have not for reasons of being tragically born after this role, then you can probably look at the picture above and understand all the same.

Jennifer Aniston

Jennifer Aniston

Almost every man has dreamed about the ‘girl next door,’ and when it comes to that stereotyped image, Jennifer Aniston has both owned it, developed it, and then patented it in her own image. A few of our favorite roles that have solidified her appeal include Friends (1994-2004), The Good Girl (2002), Along Came Polly (2004), Friends with Money (2006), Bounty Hunter (2010), and Horrible Bosses (2011).

Candice Swanepoel

Candice Swanepoel

Candice, angels wings, and Victoria’s Secret have been a staple of men’s fantasies since somewhere around 2005.

Phoebe Cates (in Fast Times at Ridgemont High)

Remember this? Phoebe Cates (Linda Barrett), a red bikini, “Moving in Stereo” by The Cars playing in the background, and a young man in a nearby bathroom playing out this fantasy until he is caught, literally, ‘red-handed’.

Jennifer Connelly

Jennifer Connelly in The Hot Spot

Jennifer Connelly was a teen dream in 1986 when she appeared in the George Lucas cult classic Labrinth, opposite of David Bowie. But her star did not fade from there, taking on many more memorable roles in film, such as The Hot Spot (1990) pictured above. And she is proud of every nude scene that she has ever filmed (including Requiem For a Dream) and she would not hesitate to do them all over again – and we, well, would not hesitate to watch.

Lindsay Lohan

Lindsay Lohan

Linsay Lohan has given us many moments over the years; Some with underwear and others without. And some of them have been good, including her role in Mean Girls (2004) and a few of our favorite sexy covers in Maxim, GQ, Rolling Stone, and Photographer.

Carmen Electra

Carmen is a better fantasy than anything else, which is why we’d almost hate to spoil your favorite dreams with the joy kill of too much reality, but you can read our version of her rollercoaster life story here.

Marisa Tomei

My Cousin Vinny (1992)

She has grown in our fantasies from the character Mona Lisa Vito in the 1992 film, My Cousin Vinny, to the sexy but albeit frustrated girlfriend in Anger Management (2003). In fact, the only thing that Marisa regrets from the last several years is starting up “mom roles,” which in Hollywood, is a non-stop elevator plunge once you step aboard and close those doors.

Lucy Pinder

In 2003, Lucy Pinder was discovered at the tender age of 19. You might remember her from FHM’s 2005 “100 Sexiest Women in the World”, in which she was placed as number 16. Unfortunately, by the time 2007 came around Lucy was just barely hanging in at #92. Talk about moving in the wrong direction. But no worries Lucy, you had already cast a permanent place in our hearts.

Michelle Pfeiffer

B.A.D. Cats (1980)

Michelle Pfeiffer’s career has spaced the last 3 generations and is still going strong. Starting with B.A.D. Cats in 1980 Pfeiffer struck our fantasies with quite a few additional highlights, including Scarface (1983), Dangerous Liasons (1988), Batman Returns (1992), What Lies Beneath (2000), and we’ll let your own fantasies fill in the rest.

Kate Upton

Kate Upton bikini

I guess you could say that bikinis are kind of Kate Upton’s thing. There has really been no ‘one’ iconic bikini moment that has burned into the fantasies of many men, but rather a collection of many Sports Illustrated covers, film cameos, and random photos with really happy men standing around in the background.

Bettie Page

Betty Page is the original pinup girl, and while her legacy kicked off in the 1950s, it was rekindled in the 1980s and then thankfully never fizzled out. Her life story has been shared in everything from books, documentaries, magazine articles like this to even a broadway-style musical.

Jill St. John

DIAMONDS ARE FOREVER (1971)

While the name may not ring a bell right away, the film, (James Bond) Diamonds Are Forever (1971), made her character, Tiffany Case, a legend for wearing – you guessed it, a bikini. And she wore it through pretty much the entire film (and wore it well).

Brigitte Bardot

The Girl in the Bikini (1952)

Brigitte has lived life as she wanted. Well, perhaps not initially. Her earliest films (Crazy for Love, The Girl in the Bikini, His Father’s Portrait, Act of Love) painted her as a ‘sex kitten,’ which is the image that she will be forever depicted as through the Hollywood lens. However, the real Brigitte loved animals more than her own fame and she left the business in 1970 to start living life as she always dreamed – now that’s sexy.

Brook Shields

THE BLUE LAGOON 1980, (c) Columbia

Yeah, we know, you can’t have any conversation about the fantasy women of the 1980s without unleashing the controversial nude sexuality of an only 14-year-old Brooke Shields in the film Blue Lagoon. And our innocent adolescent eyes will never be the same because of it.

Also see:

Top 8 Male Sex Fantasies

About Max

Single and sexy. Hello ladies..



About Max Green

Single and sexy. Hello ladies..