Many men would kill to have Hugh Hefner's lifestyle. At age 90, Hefner gets more action than your average red-blooded American male. After launching his signature magazine Playboy in 1953 (which came after Hefner left Esquire for being denied a $5 raise), Hefner quickly became the king of acceptable smut. It was not always an easy road. Because of Charles Beaumont's  short story "The Crooked Man," Playboy received thousands of angry letters denouncing Beaumont and his stance against the oppression of homosexuals. Later, in 1963, Hefner was tried for obscenity after publishing nude and semi-nude photos of actress Jayne Mansfield.

Hefner survived this turbulence, but with the coming of easily accessible Internet pornography, Playboy has taken a shellacking. As evidence, in 2016, the magazine has since stopped publishing nude pictorials. Hefner's reputation has similarly taken a major hit thanks to former Playmate Holly Madison's tell-all book, Down the Rabbit Hole. This book, along with other personal accounts from former Playmates, shows just how cancerous Hefner has been for the careers of several centerfolds. The following fifteen ladies arguably suffered the most from their association with Playboy and Hugh Hefner.

15. Lindsay Lohan

In fairness to Hefner and his magazine, when Lindsay Lohan appeared nude in the January/February 2012 issue, her career was already on a major downturn. In 2007, the starlet was arrested for driving under the influence. She subsequently went in to a 45-day rehab, which also cost her at least one film role. In that same year, Lohan went into another rehab facility following appendix surgery. By 2012, Lohan was more infamous than famous, with people being more familiar with her extracurricular activities than her acting.

So, when Lohan posed nude for Hefner, the goal was probably to kickstart her career again. Lohan channeled Marilyn Monroe, Playboy's first ever centerfold, during her photo shoot. Unfortunately, although Lohan's issue apparently broke sales records, her appearance has done little to revitalize her standing in Hollywood.

14. Taryn Manning 

Playboy billed their April 2011 issue as the "Sex & Music Issue." Taryn Manning appeared on the cover because she is the lead singer of the little-known band Boomkat. However, readers then and now know Manning best as an actress. Until her career was resurrected thanks to the hit Netflix show Orange Is the New Black, Manning mostly received roles in Z-grade stinkers like The Devil's Tomb and The Perfect Age of Rock 'n' Roll. Her appearance in Playboy did very little to breathe new life into either Manning's film or musical career. As evidence of this, it's safe to say that a majority of people, even those who closely follow pop culture, have no idea that Manning ever appeared as a centerfold. The April 2011 issue is far from Hefner's highest selling product.

13. Shannen Doherty 

When she first posed nude for Playboy in March 1994, Shannen Doherty's career had already reached its highest peak. Well known for playing Brenda Walsh on the hit television show Beverly Hills, 90210, Doherty had been written off of the show by 1994. Following this, Doherty's stock began to decline and she started appearing in bad made-for-TV films. Until her brief and successful tenure with the television show Charmed, Doherty was considered damaged goods.

Almost a decade later, in December 2003, Doherty re-appeared on the cover of Playboy. This time her appearance proved even more disastrous, for this second appearance did little to nothing to help Doherty's struggling career. Sadly, Doherty is today battling a very aggressive form of cancer.

12. Carmella DeCesare 

Cleveland area native Carmella DeCesare went from being Playboy's Miss April 2003 to the Playmate of the Year in 2004. These are the highest accolades that DeCesare has ever reached. Following her flirtation with fame thanks to Hefner's magazine, DeCesare briefly worked for the WWE. In 2004, DeCesare participated in the second Divas Search and actually made it to the finals. Despite this, DeCesare's brief feud with the winner Christy Hemme is widely forgotten now. According to other contestants like Maria Kanellis, DeCesare participated simply for the money and the chance to be on TV. This did not endear her to the WWE crew at all.

In 2004, DeCesare was arrested for assault after getting into a bar fight with a woman named Kristen Hine. DeCesare claimed that her boyfriend Jeff Garcia, then the quarterback for the Cleveland Browns, was having an affair with Hine. In January 2005, DeCesare was charged with violating a restraining order and was sentenced to community service. Now a mother, DeCesare wants to distance herself from her Playboy past.

11. Chloe Amour 

In 2013, an unknown model by the name of Chloe Amour posed nude for Playboy. Amour's photoshoot was mostly relegated to the magazine's online presence, but nevertheless her pictorial turned some heads. When someone gets a reaction like that, Hollywood or appearances on television usually follow. No such thing happened with Amour.

Today, Amour works in the adult entertainment industry. Because she works under the same name that she used for her Playboy shoot, it's likely that Hefner wants nothing more to do with Amour. Hefner's animus towards "hardcore" pornography is well-documented. Other models have also become a persona non grata like Amour because of their choice to do porn. Of course Playboy is a tad bit hypocritical here, for famous porn star Sasha Grey appeared on the cover of the magazine's October 2010 issue.

10. Teri Weigel

Terri Weigel's career enjoyed a nice little boast after her first appearance in Playboy in November 1985. By the next April, Weigel, a young model from Florida, was named Playmate of the Month. Between 1985 and 1988, Weigel appeared in numerous videos produced by Playboy, and also had small roles in the films Predator 2 and Marked For Death. Weigel was also successful on the small screen and appeared as the character Jade in several episodes of Married...With Children.

It's likely that Weigel's standing with Hefner began to decline when she also appeared in Penthouse, a rival publication. Then, starting sometime in the late 1980s or early 1990s, Weigel began working at the Moonlite Bunny Ranch brothel. Weigel is better known for her long career as a pornographic actress. This career decision not only cost Weigel her relationship with her family, but because Weigel continued to use the Playboy logo on her website, Hefner sued her in 2000.

9. Kendra Wilkinson

Along with co-stars Holly Madison and Bridget Marquardt, Kendra Wilkinson was part of the E! reality television show The Girls Next Door. The show focused on the lives of these three centerfolds inside of the Playboy Mansion in Los Angeles. The show, which made a big deal out of the fact that all three girls were romantically attached to Hefner, attempted to depict life inside of the private kingdom of Playboy as blissful. However, as Madison reveals in her book, the truth was much darker.

As for Wilkinson, her life after The Girls Next Door has been rough to say the very least. First, the California tomboy married Hank Baskett, a former wide receiver for the Philadelphia Eagles. Between 2009 and 2012, Wilkinson's rocky marriage was documented as part of the reality show Kendra, which also aired on E! Wilkinson continues to appear on television, this time on the WE TV show Kendra on Top.

In the real world not covered by TV cameras, Wilkinson has made headlines for her crude antics and penchant for getting into fights. Just recently a drunken Wilkinson nearly came to blows with another passenger on board a flight bound for Los Angeles.

8. Holly Madison

Holly Madison probably doesn't get a Christmas card from Hefner every year. Although she was his girlfriend for a number of years, Madison's exposé of the true Playboy lifestyle in Down The Rabbit Hole paints Hefner and his empire as a sick, venal playground that is no better than a prison. Indeed, Madison claims in her book that she felt that the mansion's gates kept her locked inside and away from the outside world.

Down The Rabbit Hole chronicles Madison's descent into depression, alcoholism, and drug use. She blames all of these bad habits on the "ridiculous" lifestyle that she led as Hefner's "Girlfriend No.1." Because of all of the strict rules and because the Playboy Mansion fostered a type of environment only comparable to William Golding's Lord of the Flies, Madison finally decided to leave. To make her decision truly final, Madison had her Playboy logo tattoo removed. Today, Madison is a mother who tries to keep out of the limelight.

7. Jill Ann Spaulding

Long before Holly Madison published her tell-all book, former Playmate Jill Ann Spaulding revealed all of Playboy's dirt in her 2004 book Jill Ann: Upstairs. The book is full of salacious revelations. In one instance, Spaulding claims that sex with Hefner is almost always unprotected. The aged magazine impresario doesn't even bother to get his girlfriends tested before engaging in intercourse. Hef's girlfriends must have sex with him, and Spaulding spares no details in comparing intercourse with Hefner to a bizarre ritual. Apparently, after swallowing a Viagra, Hefner lies motionless on the bed while a chorus of Playmates circle the bed and cheer him on.

Jill Ann: Upstairs certainly did not endear Spaulding to either Hefner or the people who work for him. Since 2004, nary a peep has been heard from Spaulding. Her career is essentially DOA.

6. Bai Ling

Chinese-born Bai Ling was  a hot commodity when she appeared in the pages of Playboy in June 2005. However, her decision to pose nude for Hefner would prove to be fateful. Although George Lucas has denied it, many people believe that Ling's role in Star Wars: Episode III -Revenge of the Sith was cut from the final release because of her nude photoshoot.

Since the mid-2000s, Ling has made a name for herself as a human train wreck. In 2008, Ling was arrested at LAX for shoplifting. Ling told E! that her decision to steal was based on a recent break-up. A few years later, Ling told an interviewer that she was originally from the moon. Such bizarre antics were explained when Ling appeared on the show Celebrity Rehab with Dr. Drew. Ling went on the show to overcome her dependence on alcohol. For the majority of that season, Ling was not depicted favorably.

5. Chyna

While at the height of her fame as a professional wrestler, Chyna (real name Joanie Laurer) posed nude for Playboy and appeared on the cover of the November 2000 issue. This issue proved to be so popular that Chyna did a second photoshoot for the magazine in 2002. Not long after this, Chyna's career took a tragic nosedive.

After leaving the WWE in 2001 under a black cloud (Chyna later claimed that she was forced out by her former boyfriend Triple H because of his new relationship with Stephanie McMahon), Chyna appeared in a sex tape alongside her then boyfriend and fellow professional wrestler X-Pac (real name Sean Waltman). This video, called 1 Night in Chyna, apparently earned the couple thousands of dollars. However, Chyna maintained in the media that she never received any financial benefits from the video's release. Although her first foray into adult entertainment clearly upset her, Chyna would later become a professional porn star in the late 2000s. This career decision is likely what kept her out of the WWE Hall of Fame. On April 20, 2016, Chyna passed away as the result of a drug overdose.

4. Izabella St. James 

Like a lot of Hugh Hefner's former girlfriends, Izabella St. James is a stunning blond. The Polish-born St. James first met Hefner in the autumn of 2000. Soon thereafter, St. James began traveling around as a member of Hefner's entourage, or rather his harem of young and attractive women. By 2002, St. James was one of Hefner's girlfriends and a resident of the Playboy Mansion. She didn't leave until 2004.

Two years after breaking up with Hefner, St. James published Bunny Tales, a tell-all account of her life inside of Hefner's mansion. St. James's autobiography makes several startling claims. In one instance, St. James relates how every Friday morning, she and the other girls would first have to clean up dog poop off of Hefner's carpets before they could receive their weekly allowance of $2,000. Sometimes Hefner would withhold this allowance if he felt certain girls weren't being active enough during his mandatory sex sessions.

In another instance, St. James claims that Hefner would regularly feed his girlfriends Quaaludes in order to "get them in the mood." Surprisingly, although both of their books reveal the ugly side of Playboy, St. James has publicly called Holly Madison a "weirdo" who once had an unhealthy obsession with Hefner. Nowadays, St. James occasionally appears on reality TV shows in her native Poland.

3. Pia Reyes

In November 1988, Pia Reyes was named the Playmate of the Month. Reyes is one of the few Asian models to ever be given this honor. Even more specifically, Reyes is one of the few Filipino models to ever grace the pages of Playboy. Reyes capitalized on this success by starring in the indie horror film Return of the Living Dead 3 in 1993. The very next year, Reyes starred alongside Steven Seagal in On Deadly Ground. 

Unfortunately for Reyes, her decision to marry to the French criminal Christophe Rocancourt would prove to be her undoing. A professional confidence man and imposter, Rocancourt not only saddled Reyes with some of his massive debt, but the pair were charged with fraud in Canada in 2001. Police quickly determined that Reyes had not participated in her husband's activities and released her. Now divorced with one child, Reyes currently lives in New York City.

2. Anna Nicole Smith

Anna Nicole Smith was the first public disaster that caught the attention of E! A native of Mexia, Texas, Smith gained her first serious taste of fame when Playboy named her as their Playmate of the Year in 1993. The statuesque blond made further headlines by marrying the 89-year-old oil tycoon J. Howard Marshall II in 1994. Because of the drastic age difference and because, as his wife, Smith had a legal claim to some of Marshall's fortune, this marriage caused a lot of controversy, especially with Marshall's family. After Marshall's death in 1995, Smith fought E. Pierce Marshall, one of her late husband's sons, in court for years over her claim to Marshall's $1.6 billion estate.

Smith's second act came in the form of a reality television on E! (notice a pattern yet?). The Anna Nicole Show, which ran from 2002 until 2004, pretty much showed Smith to be a ditzy, often overweight, and overbearing has-been. The show was incredibly popular. When Smith died from an accidental overdose in 2007, millions mourned her passing. If you listen closely, you can hear Nicki Minaj give Smith a shoutout in Trey Songz's "Bottoms Up."

1. Dorothy Stratten

Canadian centerfold Dorothy Stratten did not live to see 21. The seeds of this crime were planted back in Vancouver, where a 17-year-old Dorothy Hoogstraten worked at a local Dairy Queen. The high school student caught the eye of Paul Snider, a man who had previously had a hand in creating the Chippendales dancing troupe. Convinced that the good-looking blonde could make him money, Snider, who worked as a pimp, decided to take Stratten to America.

Before long, nude photographs of Stratten came to the attention of Playboy's editors. In August 1979, Stratten was named Playmate of the Month. The next year she earned the title of Playmate of the Year. This honor opened up multiple doors to Stratten, who soon found herself starring in films like Skatetown, U.S.A. and Galaxina. Stratten's public success did not spill over into her personal life, however. Because of his controlling ways and his monstrous temper, Stratten began to distance herself away from Snider. At some point she began having an affair with the acclaimed director Peter Bogdanovich.

After a private investigator confirmed the affair, Snider decided that he was losing his wife and his meal ticket for good. So, on August 14, 1980, Snider shot Stratten dead with a 12-gauge shotgun. Snider then turned the gun on himself and pulled the trigger. This murder-suicide remains the most infamous episode in Playboy's history.

Sources: biography.com, forbes.com, cnn.com, browardpalmbeach.com, crimefeed.com