11 Best Celebrity Sex Tapes of All Time, Ranked by Cinematic Value
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11 Celebrity Sex Tapes, Ranked by Cinematic Value

A connoisseur assesses the salacious genre.

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I've watched a lot of celebrity sex tapes. Dozens of them. Rarely are they titillating—but more interesting is how much they do or don't offer a glimpse into the private lives of those involved. They leave you wondering: Are they being themselves? Are they acting? Are they acting well? Why did they choose the kitchen? When you're filming your sexual activities, self-presentation is paramount.

After watching a few of these, you can easily spot the frauds, whose construction is manipulated down to the last frame (see: Kim Kardashian, who now has the best-selling sex tape of all time). As in Kardashian's case, a sex tape can skyrocket someone to fame (or at least infamy); on the other hand, a sex tape can ultimately bring ruin to an independent media company (*cough*Hulk Hogan*cough*).

Considering this is pornographic genre of great cultural interest, I've ranked 11 pivotal celebrity sex tapes here from best to worst—as measured purely by their cinematic qualities.

Note: Esquire does not endorse theft or unpermitted distribution of copyrighted material, but these have all been widely circulated, commented upon, and in some cases publicly approved and/or mocked by the participants.

11. Rob Lowe (1988)

10. Rob Lowe (1988)

This is one of the earliest and most notorious celebrity sex tapes, having nearly ruined Lowe's career. Watching it is a dull and queasy task. It's filmed from an unlevel tripod in yellowy light (gotta remember that white balance) and filled with white noise and blurry group sex whose indistinctness only leads you to imagine the worst. Alas, the '80s were not as glamorous as previously reported.

10. Dustin Diamond (2006)

9. Dustin Diamond (2006)

No one asked Screech for a sex tape. But Screech felt like unleashing one upon the world, and the result is even more nausea-inducing than one might expect. Diamond films two women from central porn casting, asking them, "Do you want to see the monster?" He later admitted that he used a "stunt wang." Sounds about right.

9. Fred Durst (2005)

8. Fred Durst (2005)

Durst keeps the camera on the woman (somewhat understandably), not allowing us to take in the wider mise-en-scène and forcing us to identify him by his sleeve tats, before an abrupt mid-video pan to his face in closeup. This is just sloppy filmmaking, especially from a veteran music video director.

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8. Paris Hilton (2004)

7. Paris Hilton (2004)

There are about as many Paris Hilton sex tapes as entries in the Hunger Games franchise. None of them is pleasant. The most famous, One Night in Paris, is a textbook example of everything you shouldn't do with your home porno. It's introduced by sleaze Rick Salomon himself, who thinks more highly of his skills than he should (his creepy catchphrase: She likes it...). Hilton, meanwhile, is so bored out of her mind that at one point she stops to answer her phone. There's no fun in watching them debate where to station the camera on a table. (Tip: Handheld is almost always better than stationary photography, especially webcams, which feel distant and clinical.) And the video makes a compelling case for never using the night vision setting to film your own sex, thereby giving it the dreaded Blair Witch/Zero Dark Thirty effect. At one point Salomon, chewing gum and staring at a monitor displaying his own cock, comments, "It looks like we're having a good time." No, it doesn't, Rick. It really doesn't.

7. Farrah Abraham (2013)

Bikini, Lingerie, Clothing, Undergarment, Swimwear, Brassiere, Swimsuit bottom, Model, Navel, Swimsuit top,

It's hard to feel good about Farrah Superstar: Backdoor Teen Mom. She was a former teen mom, now a regular mom craving publicity. He—he being famed porn star James Deen—has been accused of rape and sexual assault by multiple women. Abraham claimed the tape was a leak. Turns out she made $1.5 million for selling it to Vivid Entertainment. But, technically speaking, this production could have been worse. It was even good enough to spawn a sequel, Farrah 2: Backdoor and More. So there's that.

6. Gene Simmons (2008)

6. Gene Simmons (2008)

Befitting its star, this is just out-and-out weird. Simmons enters to Foreigner's "I Want to Know What Love Is" as a candle flickers in the background. He wears only a t-shirt (never a good look for a guy), and the woman seems game for anything but kissing him. The faraway stationary black-and-white photography works, for once, lending a surreal vibe to the proceedings.

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5. Kim Kardashian and Ray J (2007)

5. Kim Kardashian and Ray J (2007)

It's rigorously controlled, with annoying soundtrack cues, though that should surprise no one who has followed Kardashian's career. In many ways this is the earliest glimpse into her ability to exploit her own bodily gifts for monolithic public attention. She shows little interest in the sex, but defends the naturalness of her breasts to the camera and insists that Ray J record her "bling" all the way down to her feet. She shows the slightest bit of humanity when Ray J shoots her unpacking, but it's quickly replaced by a smile. Kardashian is a pro.

4. Hulk Hogan (2012)

4. Hulk Hogan (2012)

Hogan's tape appears to be recorded by a security camera like some kind of voyeuristic Steven Soderbergh experiment. You can't see much, but the surprisingly clear audio and subtitles suggest a gentlemanly encounter, ended by Hogan giving the woman a goodnight kiss and telling her, "You're awesome."

3. Pamela Anderson and Bret Michaels (1998)

3. Pamela Anderson and Bret Michaels (1998)

It doesn't hold a candle to her magnum opus with Tommy, but Pam as always is a master of the costume. Here she's wearing knee-high boots in a Stevie-Nicks-sex-goddess look. You nearly forget Bret Michaels is in the room.

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2. Colin Farrell (2006)

2. Colin Farrell (2006)

Farrell lays on the charm thick, which might be annoying if he didn't do it so well. He improvises increasingly inventive compliments for model Nicole Narain in his Irish lilt: "If a fucking camera could blush, this thing would be fucking red." "I didn't know they made bastards as sexy as you." And best of all: "Breakfast, lunch, and dinner right here." He could've turned on a couple more lights, and he's probably drunk, but who wouldn't be? Bonus points for self-deprecating jokes about his crummy photography and pubic hair.

1. Pamela Anderson and Tommy Lee (1995)

1. Pamela Anderson and Tommy Lee (1995)

This is the ur-celebrity sex tape, what you might call the Citizen Kane of famous people screwing, which ushered in the form's modern era. There's little you can say about this video that hasn't already been said. So I'll say this: It's sweet. You actually feel badly that the marriage didn't work out. Pam and Tommy were clearly in love during their honeymoon. They make the most of their locations—in front of a mansion, driving in a car, on a yacht, swimming in a lake—as well as the now-nostalgic analog video camera, including an artful zoom into the MAYHEM tattoo on Tommy's stomach. They unironically call each other "lover" and show the appropriate level of bashfulness. There's even suspense when they almost hit a rock (not a euphemism, a literal rock). What you get is what you want from any movie: a journey. Emotional, uh, payoff. There are few moments in cinema as tender and sincere as when Pam says, "He's gotta get me through the rest of my life." Granted, she's talking about Tommy's junk, but that's how true love works, isn't it?

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