Long before E! came out with The Girls Next Door series, the world had already become accustomed to seeing Hugh Hefner surrounded with a plethora of blonde beauties on his arm. Known for walking the red carpet with more than one “girlfriend” with him, somehow the public just accepted the fact that he was not only dating women a third of his age but also dating multiple women at the same time. While it was easy for the world to look at these women as opportunistic users that were just with him for the money and fame, people seemed to still be interested in what was really going on behind the scenes. When The Girls Next Door series began, people obviously came in with preconceived notions of all the women. Yet, somehow their personalities and the inner workings of the Playboy Mansion seemed to win over viewers.
People actually became invested in the lives of Holly Madison, Bridget Marquardt, and Kendra Wilkinson. From their quirky personalities to their completely over-the-top lifestyles, the series gave a sneak peek behind the veil of the famed Playboy Mansion. Yet, it wasn’t just the three girlfriends that were highlighted in the series. There were a number of different people that were shown in the series, with each having their own stories to be told. While the series lasted for six seasons, the popularity of the characters helped to spawn a number of spin-off shows. Yet, people still wonder about all of the most memorable characters from The Girls Next Door. Check out our list of the 15 stars that were featured on The Girls Next Door, and see what some of these memorable characters have been doing since their time at the Playboy Mansion.
15 Carmella DeCesare
Carmella DeCesare was highlighted in a number of different episodes in The Girls Next Door since she was very close friends with all of Hefner’s girlfriends. During Season 1 of the show, all three of the girls flew to Las Vegas to celebrate DeCesare’s birthday. The episode divulged a lot about the intricacies involved in being one of Hef’s girlfriends, since the girls were not allowed to spend the night. A little known fact about being one of Hef’s girlfriends was that he had a strict 9 o’clock curfew, and didn’t allow his girlfriends to spend the night anywhere besides the Playboy Mansion. Unfortunately, there was a delay on their plane, and the girls wound up getting back to the Playboy Mansion past curfew. However, it does say a lot that the girls were willing to risk their day trip just to celebrate DeCesare’s birthday. Capitalizing on her time on the show and being named Playmate of the Year in 2004, DeCesare went on to participate in the WWE Diva Search competition, but is probably best known for her marriage to NFL quarterback, Jeff Garcia. Nowadays, she spends her time with her family and her devoted charity work.
14 Sara Jean Underwood
Sara Jean Underwood was introduced during the first season of The Girls Next Door. She was just one of many “new girls” that were brought in to be photographed as a test to be in the magazine. Since this is an occurrence that happens monthly, naturally, the girls of the house were guarded in how well they would receive them. Yet, there was something special about Underwood. She was later chosen to be Playmate of the Month in July 2006, and even went on to become Playmate of the Year in 2007. Her humble Oregon roots and great rapport with the ladies definitely had something to do with her success at Playboy, and she used this success to become the host of the television series, Attack of the Show!, as well as a few film appearances. Yet, many of her roles have been forgettable, even though she was cast as the lead role in the 2013 film, Deadly Weekend. She has also been a bit unlucky in love, even though she’s dated some high profile men. In the meantime, she will probably always be remembered for her portrayal as the fresh-faced newbie from The Girls Next Door.
13 Tiffany Fallon
Tiffany Fallon had a number of accolades throughout her time with Playboy from being Ms. December to being chosen as Playmate of the Year in 2005. During the very first season of The Girls Next Door, the second episode was dedicated to Fallon. It was the day of her big ceremony where she was introduced to the press, and commemorated the day that her issue hit newsstands. Holly Madison referenced her as “a good friend of ours,” so naturally, she made it onto the show. Her December spread for the magazine highlighted her ebony hair, which was a big change from the typical blonde bombshell the magazine is mostly known for. Since her time in the limelight in the magazine and on the show, Fallon had a few appearances that made people remember how beautiful she was to start with. Yet, there wasn’t much that ever came of it. In 2008, she appeared on The Celebrity Apprentice, but unfortunately, she was the first to be fired by Donald Trump. Regardless, she still makes the occasional appearance on the red carpet, and it’s clear to see that she has managed to hang onto her Playboy good looks.
12 Brittany Binger
Brittany Binger didn’t fit the typical mold as a Playboy centerfold since she had the dark hair and dark eyes. Yet, there was a natural sexiness about her that exuded sensuality unlike many of the other homespun looking girls. She was featured in a number of different episodes in The Girls Next Door series, with many involving party gatherings at the Playboy Mansion. From the Mardis Gras party in Season 3 to the Super Bowl party in Season 5, Binger was a regular among the Playboy crowd. Binger was named Playmate of the Month in June 2007, and has managed to keep her smoldering good looks since then. Unlike other former Playboy centerfolds that let themselves go downhill after their fleeting time in the Playboy spotlight, Binger has proved that her stellar good looks are more than just right for a skin magazine. She has been represented by Elite Models and Ford Models, and even transitioned as a supporting cast member on Kendra Wilkinson’s spin-off show, Kendra.
11 Mary O’Connor
The Playboy Mansion was a unique residence for more reasons than just the onsite zoo and the infamous grotto, since it managed to have two distinctly different personas. While the public liked to think of it as a nonstop party house with orgies galore (which sometimes it was), the girls living at the Playboy Mansion thought of it as their home. This was made even more true with the lovable Mary O’Connor working there. The Girls Next Door always made sure to show O’Connor working in her cozy little office, and offering motherly advice to all the girls. Unfortunately, O’Connor passed away in January 2013. She was the personal secretary of Hugh Hefner for more than 40 years, and her passing was a loss felt by all who knew her. Bridget Marquardt gave an interview with HollywoodLife.com soon after her passing and stated, “She was a dear friend, one that will never be replaced, and she will be missed.”
10 Brian Olea
While there was a veritable village that was needed to make the Playboy Mansion run smoothly, it was Brian Olea that seemed to be the man behind the machine. As a mansion staffer, he was highlighted throughout the series, and can be seen going above and beyond for the ladies. While Hugh Hefner didn’t seem to appreciate him very much, the ladies all seemed to have a close relationship with him and a very friendly rapport. When Kendra wanted a beach ball while sitting in the stands, it was Olea that went out of his way to make sure she got it and then he even saved them to decorate her door for her birthday. It’s those little things that proved how much he cared about going above and beyond for his job, and helped to make the Playboy Mansion a true home for the girls. After The Girls Next Door concluded in 2010, Olea became the co-host of Mansion Mayhem on PlayboyRadio.com but pretty much stayed out of the limelight afterward. Nowadays, he pops up occasionally via a fan picture when out and about, but life has certainly changed for him after the sale of the Playboy Mansion.
9 Barbi Benton
The obvious elephant in the room regarding The Girls Next Door was the fact that Hefner’s girlfriends were far younger than him, and looked more like his grandkids rather than his sexual companions. Yet, Hefner has had a long history of dating much younger women, even before he could be considered a senior citizen. In fact, back when he was 42-years-old, he began pursuing 18-year-old, Barbi Benton. The two actually had a long-lasting relationship back in the day, and she was highlighted on The Girls Next Door on a number of occasions. She seemed to have an ultra-close relationship with Hefner, which was a great storyline involving the jealousy element with head girlfriend, Holly Madison. The entire crew even stayed at Benton’s lavish home during the series, and it showed that Benton didn’t end up shabbily after she and Hefner split ways. However, her marriage to real-estate mogul, George Gradow, wasn’t exactly a picture-perfect situation, since he wound up getting sentenced to 15 months in prison for tax fraud in 2006. Nowadays, she obviously no longer looks like her 18-year-old self, but she doesn’t even look the same as when she was featured on The Girls Next Door. Time has marched on for Benton, and she is definitely looking her age.
8 Destiny Davis
Destiny Davis was highlighted on a number of episodes in The Girls Next Door, and seemed to be good friends with all of the girls in the house. However, she was closest with Kendra Wilkinson, and the two can be seen hanging closely together early on in the series. While she held the title of Playmate of the Month in January 2005, she definitely didn’t seem like a favorite of Hugh Hefner. In fact, in one episode of the first season, Hefner can be seen scolding Davis for her excessive drinking on the party bus and even states, “You better pace yourself.” Davis was one of the biggest party girls on the series, and was everyone’s go-to girl for having fun. Davis wound up marrying Las Vegas businessman, Chad Elie, in a hurried Vegas wedding the day after he was indicted with 10 other defendants in charges stemming from online gambling. Her 7,200 square foot home was seized after the crackdown with the U.S. federal government. This definitely doesn’t seem like a winning result for this former Playboy Mansion beauty.
7 Valerie Mason
By the time Season 4 rolled around for The Girls Next Door, Holly Madison had a much deeper involvement in the magazine and was given the job of Assistant Photo Editor/Playmate Editor. While she seemed to still think that her progression in the magazine was utterly glacial, it should have meant a great deal that she had the ability to invite four potential Playmates to shoot test photos for the magazine. Among the potential candidates, Valeria Mason arrived and made quite an impression on viewers. Although she didn’t have the typical blonde-haired look like the other Playmates, she did have a certain girl-next-door look that transferred well to the camera. Her jet black hair and ample assets were just an added plus, and were definitely part of the deciding factor that got her chosen among the other girls as the newest Playmate. However, her time in the limelight as the September Playmate of the Month in 2008 was pretty much the pinnacle of her career, and nowadays, her star has all but fizzled out. Unless the various adult entertainment blog sites count as added exposure, Mason wasn’t one of the winners that came out of The Girls Next Door.
6 Kristina Shannon & Karissa Shannon
Although twins, Kristina Shannon and Karissa Shannon, were shown on The Girls Next Door series prior to becoming one of Hugh Hefner’s girlfriends, it wasn’t until their introduction on Season 6 of the series that fans truly got to meet them. The episode entitled, “Meet the New Girls” starred Karissa, Kristina, and Crystal as the new girlfriends of Hefner since all three of the former girlfriends had moved on. Playboy has always had a fascination with twins, triplets, and even mother/daughter personas, so it shouldn’t have come as a surprise that Hefner would date two identical twin sisters. Whether the public didn’t take kindly to the former girlfriends being replaced so immediately or the twins didn’t have the same engaging personality as the others, their time on the show (or on Hefner’s arm) was limited. Season 6 was the final season of the show, and Hefner dropped the twins to be exclusive with Crystal Harris. Since their time on the series, both of the twins engaged in some pretty tawdry behavior including a sex tape with Spencer Pratt and Heidi Montag. Yet, things got really interesting when the twins were seen on an episode of Botched. Their 2015 appearance was shocking to fans of the series since both twins looked completely different due to botched plastic surgery and an exorbitant amount of weight gain.
5 Crystal Harris
Crystal Harris was introduced as one of Hugh Hefner’s newest girlfriends in the opening of Season 6, and seemed to replace Holly Madison as the new head love interest. While the twins had their appeal due to the male fascination with hot twins, Harris seemed to be more “in love” with Hefner and striving for a true relationship with the Playboy mogul. In many of the Season 6 episodes, Harris can be seen crafting scrapbooks for Hefner and acting more like a personal assistant than a romantic partner. Once the series concluded, the two actually became engaged, which was a shocker to everyone who thought of Hefner as a serial bachelor (especially former girlfriend, Holly Madison). Harris wound up breaking off their engagement and gave an infamous 2011 interview with Howard Stern where she said she was “not turned on” by Hefner and he lasted “two seconds.” The two wound up reconciling, and nowadays she gives interviews on how happily married they are.
4 Kendra Wilkinson
Kendra Wilkinson was the youngest girlfriend in their threesome, and famously won over Hugh Hefner from a random photo he came upon while in the Playboy Mansion. She was working as a painted lady for one of the Playboy Mansion’s infamous parties, and the rest is history. She moved in within a week of meeting Hefner, and seemed like the girlfriend that at least had a connection with him. However, he was noticeably enamored with her, and seemed to give her leniency that the other two girls didn’t get. Wilkinson wound up splitting with Hefner and ultimately married former NFL football player, Hank Baskett. The two had their own reality television show, which gave attention to other The Girls Next Door Playboy models. However, things didn’t turn out well for Wilkinson due to a number of public snafus. Two sex tapes came out involving Wilkinson prior to her relationship to Baskett, and then a transvestite came out to declare that there was a sexual relationship with Baskett. All of this drama played out on the reality show, and nowadays, the public sees Wilkinson as the long-suffering Playmate that can’t seem to catch a break.
3 Bridget Marquardt
Bridget Marquardt was arguably the most interesting of Hugh Hefner’s girlfriends since she had a completely different background than any of the other girls. While some of the other girls were nervous about taking it all off for the magazine, Marquardt revealed that she had been dreaming about posing for Playboy ever since she was 5-years-old and would skim through her father’s Playboy magazines. She was also highly educated and even had a Master’s degree, while some of the other girls could barely spell “educated.” After she left The Girls Next Door series, Marquardt began dating director, Nick Carpenter, and the two became engaged. He famously proposed with a spider-shaped diamond engagement ring, which she has claimed was the perfect ring he could have given her. The two supposedly are big on themes and Halloween, and the ring was a representation of those things that the two have in common. In the meantime, Marquardt has pretty much stayed out of the headlines and seems to be very much in love.
2 Holly Madison
As the head girlfriend in The Girls Next Door, fans always imagined that she and Hefner would one day make their union monogamous. It seemed that she truly did love and have a real connection with Hefner, unlike any of the other girls. Yet, her focus seemed to expand as the series drew on, and she seemed to be more interested in gaining a career at Playboy rather than a husband. Hefner was very vocal about his issues with marriage and not wanting to have more children, and the pair ultimately split. Afterward, Madison became romantically linked to Criss Angel and she starred in the Las Vegas show, Peepshow. The relationship with Angel fizzled out, and she had to leave the Peepshow production once she became pregnant with her boyfriend Pasquale Rotella's child. The two were married in 2013, and they had another child together. Yet, the real story involves her tell-all book entitled, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny. Madison told all the dirt about her relationship with both Hugh Hefner and Criss Angel and gave some extremely damning information that made for a salacious bestseller.
1 Hugh Hefner
Although the show may have been entitled, The Girls Next Door, the real star of the show was definitely Hugh Hefner. The man behind the myth, Hefner had the uncanny ability to still draw in young, blonde women regardless of his age. Women flocked to him throughout the series, celebrities pandered to visit the Playboy Mansion, and every single photo put into the magazine still had to be given final approval by Hefner himself. Once the series concluded, Hefner dealt with a number of public snafus including various ex-girlfriends that talked badly about his performance in bed and demeanor in general. However, he ended up marrying his girlfriend, Crystal Harris, regardless of the fact that she was one of the ex-girlfriends that talked badly about him. Playboy also endured some troublesome times, and Hefner wound up selling the property for $100 million. The magazine also struggled in sales, and they ultimately had to change the focus to try and gain new readers. In the released statement, CEO Scott Flanders stated, “After 62 years, Playboy is putting its clothes back on. It served its purpose. When Hefner launched the magazine in 1953 nudity was provocative, and today it’s passé.”