# Jenna Jameson

Jenna Marie Massoli (born April 9, 1974), known professionally as Jenna Jameson (/ˈdʒeɪmɪsən/), is an American businesswoman, writer, television personality, and former pornographic film actress. She has been named the world's most famous adult entertainment performer and "The Queen of Porn".
Jameson started acting in erotic videos in 1993 after having worked as a stripper and glamour model. By 1996, she had won the "Top Newcomer" award from each of the three major adult movie organizations. She has since won more than 35 adult-video awards, and has been inducted into the X-Rated Critics Organization (XRCO) and Adult Video News (AVN) Halls of Fame.
Jameson founded the adult-entertainment company ClubJenna in 2000 with Jay Grdina, whom she later married and divorced. Initially, a single website, this business expanded into managing similar websites of other stars and began producing sexually explicit videos in 2001. The first such movie, Briana Loves Jenna (with Briana Banks), was named at the 2003 AVN Awards as the best-selling and best-renting pornographic title for 2002. By 2005, ClubJenna had revenues of US$30 million with profits estimated at half that.
Jameson has also crossed over into mainstream pop culture, starting with a minor role in Howard Stern's 1997 film Private Parts. Her mainstream appearances continued with several guest-hosting and guest-starring on various television programs. Playboy TV hosted her Jenna's American Sex Star reality show, in which aspiring porn stars competed for a ClubJenna contract. Her 2004 autobiography, How to Make Love Like a Porn Star: A Cautionary Tale, spent six weeks on The New York Times Best Seller list.
Jameson announced her retirement from pornography at the 2008 AVN Awards, stating that she would never return to the industry. Although she no longer performs in pornographic films, she began working as a webcam model in 2013.

## Early life

Jenna Marie Massoli was born on April 9, 1974, in Las Vegas, Nevada. Her father, Laurence Henry Massoli, was a police officer at the Las Vegas Sheriff's Department and program director for KSNV-DT. Her mother, Judith Brooke Hunt, was a Las Vegas showgirl who danced in the Folies Bergère show at the Tropicana Resort & Casino. Her mother died of melanoma on February 20, 1976, two months before her daughter's second birthday. The cancer treatments bankrupted the family and they relocated in Nevada, Arizona and Montana, usually living in a trailer home or with her paternal grandmother. She and her older brother Tony were raised Catholic, though they were essentially left to parent each other.
Jameson was a frequent entrant in beauty pageants as a child and enrolled in ballet classes throughout her childhood. In a featurette on the Zombie Strippers DVD, Jameson indicates she trained in dance for 15 years.
Jameson wrote in her autobiography that in October 1990, when she was 16 years old and while the family was living on a cattle ranch in Fromberg, Montana, she was beaten with rocks and gang raped by four boys after a football game at Fromberg High School. The incident began after she attempted to hitchhike home and she entered the car of the four boys while believing that she would be driven to her home. She reported being raped a second time while still 16 by "Preacher", her boyfriend Jack's biker uncle. Preacher has denied the rape ever occurred. Rather than tell her father, she left home and moved in with Jack in her first serious relationship.
Jack was a tattoo artist and gave her the first of a series of tattoos, one of which would become her trademark tattoo, two hearts on her right buttock. According to E!, her brother Tony, who later owned a tattoo parlor himself, added the inscription "Heart Breaker".

## Career
### Early

Jameson tried to follow in her mother's career as a Las Vegas showgirl, but most shows rejected her for not having the then-typical height of 5 feet 8 inches (173 cm). She was hired at Disneyland Resort, but she left after two months, stating concerns over the schedule and salary.
Her boyfriend Jack encouraged her to apply for jobs as a dancer, and in 1991, though underage, she began dancing in Las Vegas strip clubs using a fake identification. After she was rejected from the Crazy Horse Too strip club because of her braces, she removed them with pliers and was accepted. After six months, she was earning US$2,000 per night, before graduating from Bonanza High School.
Her first stage name as a dancer was "Jennasis", which she later used as the name of a business that she incorporated ("Jennasis Killing Co."). As for picking her permanent professional name, she said, "I had to come up with a good name. I didn't want a porno name. So I sat down, opened up the phone book and thumbed to the J's, cause I wanted it to match my first name." She saw 'James', but rejected "Jenna James" because it "sounds too porno". Right under that was 'Jameson' which struck her as being the name of the whiskey she likes and thought "Ok, that's perfect." That night at work she saw her brother and asked him what he thought of the name "Jenna Jameson". He said, "I'm drinking Jameson right now." And the name stuck after that.
Besides dancing, starting later in 1991, she posed for nude photographs for photographer Suze Randall in Los Angeles, with the intention of getting into Penthouse. After her photos had appeared in several men's magazines under various names, she then stopped working for Randall, feeling Randall was "a shark".
While in high school, she began taking drugs – cocaine, LSD, and methamphetamine – accompanied by her brother (who was addicted to heroin) and at times her father. Her addiction worsened during her four years with her boyfriend. She eventually stopped eating properly and became too thin to model; Jack left her in 1994. She weighed 76 pounds (34 kg) when a friend put her in a wheelchair and sent her to her father, who was then living in Redding, California, in order to detox; her father did not recognize her when she got off the plane.

### Pornographic film

Jameson says that she started acting in sex videos in retaliation for the infidelity of her boyfriend, Jack. She first appeared in an erotic film in 1993, a non-explicit softcore movie by Andrew Blake, with girlfriend Nikki Tyler. Her first pornographic movie scenes were filmed by Randy West and appeared in 1994's Up and Cummers 10 and Up and Cummers 11.
Of her first adult movie, Randy West said "Jenna contacted me and said she wanted to get into the XXX business, but her agent didn't want her to do porn. A month later I'm on a shoot in Woodland Hills (a San Fernando Valley section of Los Angeles), and there's Jenna. She said she wanted to get into the business, despite what her agent said. I told her if you want to just do a girl/girl scene, we can do that. She said she wanted to work with Kylie Ireland, so I set it up. When the sex started, she just fucking rocked! I knew Jenna was special right off the bat. I figured she'd be the next Ginger Lynn, but nobody had any idea she was going to be as big as she turned out to be. Jenna told me when we first met that she was going to be a star."
Jameson got her first breast implants on July 28, 1994, to enhance her stripping and movie careers.
Jameson's first adult video appearances were lesbian scenes (a common way that female performers ease into the business). She says: "Girl-on-girl was easy and natural. Then they offered me lots of money to do boy-girl." Her first heterosexual scene was in Up and Cummers 11 (1994). At the beginning of her career, she promised herself that she would never do anal sex or double penetration scenes on film. Instead, her "signature move" was oral sex, lubricated with saliva. She has also never done any interracial sex scenes with men (despite that category's runaway popularity during the 2000s).
In 1994, after overcoming her drug addiction by spending several weeks with her father and grandmother, Jameson relocated to Los Angeles to live with Nikki Tyler. Her first movie after that was Silk Stockings. Later in 1995, Wicked Pictures, a then small pornographic film production company, signed her to an exclusive contract. She remembers telling Wicked Pictures founder Steve Orenstein: "The most important thing to me right now is to become the biggest star the industry has ever seen."
The contract earned Jameson US$6,000 for each of eight movies in her first year. Her first big-budget production was Blue Movie (1995), where she played a reporter investigating a porn set; it won multiple AVN Awards. In 1996, Jameson won top awards from three major industry organizations, the XRCO Best New Starlet award, the AVN Best New Starlet Award, and the Fans of X-Rated Entertainment (F.O.X.E.) Video Vixen award. She was the first entertainer to win all three awards.
By 2001, Jameson earned $60,000 for a day and a half of filming a single DVD, and $8,000 per night dancing at strip clubs. She tried to restrict herself to five films per year and two weeks of dancing per month. Her husband Jay Grdina has said that she earned as much as $25,000 per night dancing.
Between 2005 and 2006, she hosted Playboy TV's Jenna's American Sex Star, where prospective porn stars compete in sexual performances for a contract with her company, ClubJenna. Winners of the contracts for the first two years were Brea Bennett and Roxy Jezel.
In January 2008, Jameson confirmed she was retiring from pornographic performances and has since said that she "won't even do a Maxim cover".
Jameson's first appearance at an adult-entertainment event since her retirement was at the 2013 Exxxotica New Jersey convention in October. On January 15, 2014, Fleshlight released Jameson's signature artificial vagina. Jameson was also the master of ceremonies for the 2014 XBIZ Awards on January 24.

### Business ventures

Jameson and Grdina formed ClubJenna as an Internet pornography company in 2000. ClubJenna.com was one of the first pornographic sites to provide more than pictures and videos; it provided explicit diaries, relationship advice, and even stock tips to paid members. The site reportedly was profitable in its third week. The business later diversified into multimedia pornographic entertainment, first by administering other porn stars' websites, then, in 2001, by the production of pornographic films.
Early ClubJenna films starred Jameson herself, limiting herself to on-screen sex with other women or with Grdina, who appeared as Justin Sterling. The first ClubJenna film, Briana Loves Jenna (2001), co-produced with Vivid, cost US$280,000 to make, and grossed over $1 million in its first year. It was the best selling and best-renting pornographic title of its year, winning twin AVN Awards. It was marketed as "Jenna. Her first boy/girl scene in over 2 years." referring to Jameson's abstention from heterosexual on-film intercourse. Grdina has said that Jameson's films averaged sales of 100,000 copies, compared with run-of-the-mill pornographic films, which did well to sell 5,000. On the other hand, he also said that their films took up to twelve days to film, compared with one day for other pornographic films.
In a January 2009 interview with William Shatner on Shatner's Raw Nerve, Jameson said she came close to buying Penthouse magazine when publisher Bob Guccione filed for Chapter 11 reorganization of his business (which occurred in August 2003), but was thwarted when someone else swooped in and bought up all the stock. New York Magazine's Intelligencer quoted a source from Penthouse as saying "I'm sure she is considering it", adding that Jameson was to be cover girl in January 2004 – and "it's a really wild-looking shoot, even for a porn star."
In 2004, the ClubJenna films expanded to starring other actresses without Jameson – Krystal Steal, Jesse Capelli, McKenzie Lee, Ashton Moore and Sophia Rossi – as Jameson stepped back from starring roles. In 2005 Jameson first directed a film, The Provocateur, released as Jenna's Provocateur in September 2006. The ClubJenna films were distributed and marketed by Vivid Entertainment, which Forbes magazine once called "the world's largest adult film company". They made up a third of ClubJenna's revenues, but over half of the profits.
ClubJenna was run as a family business, with Grdina's sister, Kris, as vice president in charge of merchandising. In 2005, ClubJenna had estimated revenues of $30 million, with profits of about half that.
Jameson also capitalized on merchandising herself. Since May 2003, she has been appearing on a 48-foot (15 m) tall billboard in New York City's Times Square promoting her web site and movies. The first advertisement displayed her wearing only a thong and read "Who Says They Cleaned Up Times Square?" There is a line of sex toys licensed to Doc Johnson, and an "anatomically correct" Jenna Jameson action figure. She stars in her own sex simulation video game, Virtually Jenna, in which the goal is to bring a 3D model of her to orgasm. Y-Tell, ClubJenna's wireless company, sells Jenna Jameson "moan tones" (telephone ringtones), chat services, and games in partnerships with 20 carriers around the world, mostly in Europe and South America. In 2006, New York City-based Wicked Cow Entertainment started to expand her brand to barware, perfume, handbags, lingerie, and footwear, sold through high end retailers such as Saks Fifth Avenue and Colette boutiques. Her film and merchandising success enabled her to attain her goal of becoming the top porn star in the world.
In August 2005, ClubJenna launched Club Thrust, an interactive website for Jameson's gay male fans, which includes videos, galleries, sex advice, gossip, and downloads. The director of webmaster relations for ClubJenna said the straight site had always had a lot of gay traffic. By 2006, ClubJenna administered more than 150 official sites for other adult entertainment industry stars.
In August 2005, a group of business investors that included Jameson purchased Babes Cabaret, a strip club in Scottsdale, Arizona, intending to make it the first foray of ClubJenna into live entertainment. Soon after the purchase attracted attention, the Scottsdale City Council proposed a new ordinance banning nudity at adult-entertainment venues and requiring a four-foot divider restricting contact with dancers. Such a divider would have also effectively banned lap dances, the dancers' main source of revenue. Jameson argued strongly against the ordinance, and helped organize a petition against it. On September 12, 2006, in a referendum on the ordinance, voters struck down the stricter rules, allowing the club to continue to operate as before.
On February 3, 2006, Jameson hosted a "Vivid ClubJenna Super Bowl Party" with several other ClubJenna and Vivid Girls at the Zoo Club in Detroit, Michigan for a $500 to $1,000 ticket price. It featured a lingerie show, but no planned nudity or sex acts. When first announced, the party caused controversy with the National Football League, which did not sanction this as an official Super Bowl event. For 2007, Jameson signed up to play quarterback in the Lingerie Bowl, but retired due to her insurance company's damage concerns. She instead acted as commentator.
On June 22, 2006, Playboy Enterprises announced that it had bought ClubJenna Inc., along with an agreement to have both Jameson and Grdina stay on as contracted executives. Playboy CEO Christie Hefner said that she expected to rapidly increase film production, producing about thirty features in the first year, and will expand the way they are sold, not only as DVDs but through TV channels, video-on-demand services, and mobile phones. On November 1, 2006, Playboy renamed one of the Spice Network's pay-per-view channels from The Hot Network to ClubJenna.

### Books

Jameson's autobiography, How to Make Love Like a Porn Star: A Cautionary Tale was published in 2004. It was co-written with Neil Strauss, a contributor to The New York Times and Rolling Stone, and published by ReganBooks, a division of HarperCollins. It was an instant bestseller, spending six weeks on The New York Times Best Seller list. The autobiography also won the 2004 "Mainstream's Adult Media Favorite" XRCO Award in a tie with Seymore Butts's Family Business TV series. It was translated into German as Pornostar. Die Autobiographie in November 2005, and Spanish as Cómo Hacer El Amor Igual Que Una Estrella Porno in January 2006.
The book covers her early career from her beginning in show business living with her tattoo artist boyfriend, through receiving the Pornographic Hot d'Or award at Cannes, and wedding pictures from her second marriage. It does not omit sordid details, describing her two rapes, drug addictions, an unhappy first marriage, and numerous affairs with men and women. The first-person narrative is broken up by personal photos, childhood diary entries, family interviews, movie scripts, and comic panels.
The autobiography publisher, Judith Regan, also served as executive producer of a tie-in television news special, Jenna Jameson's Confessions, airing on VH1 on August 16, 2004, one day before the book's launch. In April 2005, ReganBooks and Jameson filed lawsuits against each other. The point of contention was a proposed reality show about Jameson's everyday life, discussed between her then-husband, Jay Grdina, and the A&E Network. ReganBooks maintained that any A&E deal was a breach of Jameson's contract, which indicated that ReganBooks had a stake in the profits generated by both the special based on her memoir and a reality-based series, as well as "any similar projects". Jameson's suit claimed that the A&E deal preceded the ReganBooks contract. The reality series had still not materialized, and the lawsuit was still being discussed, when HarperCollins fired Judith Regan on December 15, 2006, over an unrelated issue.
In January 2007, Jameson was reported in talks with producers on turning the autobiography into a movie. In March 2007, Jameson was reportedly missing meetings with producers, thus endangering the movie, due to problems with a recent vaginoplasty.
In April 2013, Jameson announced she was working on a fictional erotic novel called Sugar. It was co-written with Hope Tarr and published by Skyhorse Publishing. It was released on October 21, 2013.

### Mainstream appearances

Jameson is also known for achieving a high level of celebrity outside of pornography – even bringing pornography itself closer to mainstream society's awareness and acceptance. She has said: "I've always embraced my hard-core roots, but becoming a household name was an important thing to me."
In 1995, Jameson sent photos of herself to radio host Howard Stern. She became a regular guest on his show, appearing more than 30 times, and played the role of "Mandy", the "First Nude Woman on Radio", in Stern's semi-autobiographical 1997 film Private Parts. This film appearance was the beginning of a series of non-porn film and television roles. In 1997, Jameson made an appearance for an Extreme Championship Wrestling pay-per-view, Hardcore Heaven '97 as the valet for The Dudley Boyz; another appearance at ECW Living Dangerously on March 1, 1998; and a few months where she was ECW's on-screen interviewer. In 1998, she filmed a vignette with Val Venis, a character in the WWE, for airing on WWE programming. In the late 1990s, Jameson guest hosted several episodes of the E! cable network's hit travel/adventure/party show Wild On!, appearing scantily clad in tropical locations. Jameson was featured and interviewed on the British television show European Blue Review on Channel 5.
Jameson appeared in a 2002 music video for the Eminem song "Without Me". She can be seen in bed with Eminem as one of the "two trailer park girls" (the other one is fitness model Kiana Tom) that "go round the outside". Jameson voiced an animated version of herself in a July 2001 episode of Family Guy entitled "Brian Does Hollywood". Her character won an award for acting in a porn film directed by Brian Griffin, and at the close of the episode Peter Griffin kidnaps her. In 2002, Jameson and Ron Jeremy played themselves in Comedy Central's first feature television movie Porn 'n Chicken, in the roles of speakers for a pornography viewing club. Also in 2002, she appeared in two video games, most notably voicing Candy Suxxx in Grand Theft Auto: Vice City. Her character begins as a prostitute, but goes on to become a successful pornographic actress and is displayed on several billboards within the game. Her performance won the 2003 G-Phoria "Best Live Action/Voice Performance Award – Female". She also provided both the appearance and the voice for "Daisy", a secret playable character for the video game Tony Hawk's Pro Skater 4, who performs provocative tricks with her clothing and skateboard. In 2003, Jameson appeared in two episodes of the NBC prime-time television show Mister Sterling as the girlfriend of a political financier.
In the months following the publication of her autobiography, she was interviewed on NBC, CNBC, Fox News, and CNN, and the book was reviewed by The New York Times, Reuters, and other major media outlets.
Jameson was featured prominently in Samhain, a low budget horror film in which she starred with other pornographic actresses including Ginger Lynn Allen. It was filmed in 2002 but had sat unreleased until 2005, when it was re-cut and released as Evil Breed: The Legend of Samhain. She had another minor horror film role in Sin-Jin Smyth, delayed from release until late 2006.
In February 2006, Comedy Central announced plans to feature Jameson as "P-Whip", in a starring role in its first animated mobile phone series, Samurai Love God. Mediaweek called her the biggest name attached to the project. In April 2006, Jameson was the star of a video podcast ad for Adidas, advertising Adicolor shoes by playing a provocative game of whack a mole. Jameson made an appearance in the American reality TV show The Simple Life in the fifth-season episode "Committed", broadcast on July 1, 2007; Paris Hilton and Nicole Richie, while working in a "love camp", brought her in to help throw a "love ceremony" vow for the five dysfunctional couples. In 2008, Jameson had another starring role in the comedy horror film Zombie Strippers, loosely based on Eugène Ionesco's play Rhinoceros. Madame Tussauds has a wax model of Jameson.
On August 27, 2015, Jameson became a contestant on the sixteenth series of the British reality series Celebrity Big Brother, representing the US.

#### Controversial mainstream appearances

Some of her mainstream appearances sparked controversy. An interview with Jameson contained in the 1999 Abercrombie & Fitch A&F Quarterly was part of the motivation for Michigan Attorney General Jennifer Granholm and Illinois Lieutenant Governor Corinne Wood to speak out against the hybrid magazine-catalog. The campaign was joined by parents and Christian conservative groups, and Abercrombie removed it from shelves in 2003.
In November 2001, the Oxford Union debating society invited Jameson to come to Oxford to argue against the proposition "The House Believes that Porn is Harmful." She wrote in her diary at the time, "I feel like I am going to be out of my element, but, I could never pass this chance up ... it's a once in a lifetime thing." In the end, her side won the debate 204 to 27.
In February 2003, Pony International planned to feature her as one of several pornographic actors in advertisements for athletic shoes. This was attacked by Bill O'Reilly of Fox News in an editorial called "Using Quasi-Prostitutes to Sell Sneakers", calling pornographic actors inappropriate role models for teens. In response, The Harvard Crimson proposed a boycott of O'Reilly and Fox News. Jameson herself sent a sarcastic email to the show, writing:
   I hope Bill understands the difference between a porn star and a hooker. I assume he has done some research on the subject because he requested some of my videos after we finished taping my appearance. I imagine he wanted them for professional reasons.

## Awards

| Year | Ceremony | Award | Work | Co-winners |
| 1995 | NightMoves Award | Best New Starlet | — | — |
| 1996 | AVN Award | Best Actress – Video | Wicked One | — |
| 1996 | AVN Award | Best Couples Sex Scene – Film | Blue Movie | T.T. Boy |
| 1996 | AVN Award | Best New Starlet | — | — |
| 1996 | F.O.X.E. Award | Video Vixen | — | — |
| 1996 | Hot d'Or Award | Best New American Starlet | — | — |
| 1996 | Hot d'Or Award | Best American Actress | — | — |
| 1996 | XRCO Award | Starlet of the Year | — | — |
| 1996 | NightMoves Award | Best Actress | — | — |
| 1997 | AVN Award | Best Couples Sex Scene – Film | Jenna Loves Rocco | Rocco Siffredi |
| 1997 | AVN Award | Best Couples Sex Scene – Video | Conquest | Vince Vouyer |
| 1997 | F.O.X.E. Award | Female Fan Favorite | — | Jeanna Fine & Shane |
| 1997 | Hot d'Or Award | Best American Actress | — | — |
| 1997 | NightMoves Award | Best Actress | — | — |
| 1998 | AVN Award | Best All-Girl Sex Scene – Film | Satyr | Missy |
| 1998 | F.O.X.E. Award | Female Fan Favorite | — | Tiffany Mynx, Stacy Valentine & Stephanie Swift |
| 1998 | Hot d'Or Award | Best American Actress | Sexe de Feu, Coeur de Glace | — |
| 2002 | KSEXradio Listener's Choice Award | Favorite Porn Star | — | — |
| 2003 | AVN Award | Best All-Girl Sex Scene – Video | I Dream of Jenna | Autumn & Nikita Denise |
| 2003 | Adam Film World Guide Award | Best All-Girl Sex Scene – Video | Briana Loves Jenna | Briana Banks |
| 2003 | G-Phoria Award | Best Female Voice Performance | Grand Theft Auto: Vice City | — |
| 2003 | KSEXradio Listener's Choice Award | Favorite Porn Star | — | — |
| 2004 | XRCO Award | Best Girl/Girl scene | My Plaything: Jenna Jameson 2 | Carmen Luvana |
| 2004 | KSEXradio Listener's Choice Award | Favorite Porn Star | — | — |
| 2005 | AVN Award | Best Actress, Film | The Masseuse | — |
| 2005 | AVN Award | Best All-Girl Sex Scene, Film | The Masseuse | Savanna Samson |
| 2005 | AVN Award | Best Couples Sex Scene, Film | The Masseuse | Justin Sterling |
| 2005 | AEBN VOD Award | Performer of the Year | — | — |
| 2005 | Adam Film World Guide Award | Female Pornographer of the Year | How to Make Love Like Porn Star: A Cautionary Tale | — |
| 2005 | Adam Film World Guide Award | Best Actress | — | — |
| 2005 | XRCO Award | Mainstream's Adult Media Favorite | How to Make Love Like a Porn Star: A Cautionary Tale | Tied with Seymore Butts/Family Business |
| 2005 | XRCO Award | Hall of Fame | — | — |
| 2006 | AVN Award | Hall of Fame | — | — |
| 2006 | AVN Award | Crossover Star of the Year | — | — |
| 2006 | AVN Award | Best Supporting Actress—Film | The New Devil in Miss Jones | Savanna Samson |
| 2006 | AVN Award | Best All-Girl Sex Scene – Film | The New Devil in Miss Jones | Savanna Samson |
| 2006 | XBIZ Award | Businesswoman of the Year | — | — |
| 2006 | F.A.M.E. Award | Favorite Adult Actress | — | — |
| 2006 | F.A.M.E. Award | Fan Favorite for Hottest Body | — | — |
| 2007 | AVN Award | Crossover Star of the Year | — | — |
| 2007 | F.A.M.E. Award | Favorite Performer of All Time | — | — |
| 2007 | NightMoves Award | Hall of Fame | — | — |

## Personal life

In 2004 Jameson stated that she was bisexual, and that she had had sex with 100 women and 30 men off-screen in her life, but by 2008 she described herself as "totally hetero". She has stated the best relationship she ever had was her lesbian relationship with porn actress Nikki Tyler, which she documents in her autobiography. They lived together at the start of her porn career and again before her second marriage. Famous boyfriends discussed in her autobiography include Marilyn Manson and Tommy Lee.
On December 20, 1996, Jameson married porn star/Wicked Pictures director Brad Armstrong. The marriage lasted just 10 weeks. Although they informally separated in March 1997, she remained contractually obligated to work on Wicked Pictures projects involving both of them. They legally separated and divorced in March 2001.
Jameson met former pornographic studio owner Jay Grdina, scion of a wealthy cattle-ranching family, who had entered pornographic film production after college. From 1998 until Jameson's retirement, Grdina was Jameson's only on-screen male sex partner, acting under the name Justin Sterling. They were engaged in December 2000, well before her divorce from Armstrong, and married June 22, 2003. They tried to have children from mid-2004 onwards, as Jameson had planned to retire from adult entertainment upon becoming a mother. The couple resided in Scottsdale, Arizona, in a 6,700-square-foot (620 m$^2$) Spanish-style mansion, bought for $2 million in 2002.
In October 2006, it was reported that Jameson began dating mixed martial artist and former UFC champion Tito Ortiz, whom she met on Myspace. On December 12, 2006, Jameson filed for divorce from Grdina.
Jameson announced in August 2008 that she and Ortiz were expecting twins in April 2009. On March 16, 2009, Jameson gave birth to twin boys. Jameson and Ortiz split up in March 2013. Ortiz was granted full custody of the twins.
Jameson's father died on October 2, 2010, after suffering complications from triple bypass surgery.
On May 25, 2012, Jameson was arrested in Westminster, California and charged with three misdemeanor counts for driving under the influence of alcohol or other drugs, driving with a blood-alcohol level over the state legal limit, and driving on a suspended license after her Range Rover struck a light pole. She initially pleaded not guilty to the charges, but later changed her plea to guilty. She was sentenced to three years of informal probation, ordered to pay $340 in fines, and participate in a Mothers Against Drunk Driving victim impact panel. The charge for driving without a valid license was dismissed.
As of 2014, Jameson had undergone extensive tattooing, almost completely covering both of her arms in sleeve tattoos.
In June 2015, Jameson announced that she was converting to Judaism, in order to marry her boyfriend, Lior Bitton. In October of that year, Israel's Channel 2 announced a reality television series documenting Jameson's conversion.
On August 5, 2016, Jameson announced that she and Bitton were expecting their first child together. On April 6, 2017, they welcomed a daughter, whom they named Batel.
On January 12, 2022, Jameson announced that she was suffering from Guillain–Barré syndrome, although this was later proven to be a misdiagnosis.
On February 1, 2023, Jameson confirmed in a TikTok video that she and Bitton had ended their relationship, and was in a relationship with barber and influencer Jessi Lawless. She married Lawless on May 23, 2023.
On April 17, 2024, Jameson's wife Jessi Lawless filed for annulment of their marriage after less than a year. Lawless posted a video on her Instagram explaining that "the 50-year-old former adult film star's alleged drinking led to her decision to end the marriage."