Lindsay Lohan's 10 Most Shocking Conquests

There are so many things we could list in relation to Lindsay Lohan: we could mention the amount of great early-days films she made, the amount of terrible modern day films she’s made, the number of times she’s been arrested, the number of times she’s said she was sober but wasn’t. It’s a very public classic case of a child star falling victim to the Hollywood regime. But even we were surprised when Lohan recently penned her own little black list for magazines and websites around the world to have a field day with: that list detailed the celebrities she’s slept with.

The list, published by InTouch magazine in the United States, was reportedly found in her hotel room. 36 of Hollywood’s leading men have made the list, with predictable names ranking alongside some more surprising names in Tinseltown. We’ve taken a look at the 10 most shocking names to make the list; some of these names made us girls (and some boys) very jealous of Ms. Lohan while others left us just a bit perplexed. It should be noted that unless any one of these alleged conquests decides to speak out, there is no surefire way to verify whether anything actually went down between Lohan and her listed lovers - but a little digging in the celebrity gossip archives can go a long way to making some educated guesses!

10 Benicio Del Toro

Possibly something of a wild card on our list, way back in 2006, reports surfaced of Lindsay and the significantly older Puerto Rican actor hooking up. At the time, Lindsay’s rep confirmed that she was “not dating” Del Toro but that he was a wonderful actor. Evidently however Lohan admired the actor’s talents in a more intimate surrounding. After all, just because you’re not dating, it doesn’t mean nothing happened, right? Del Toro has not commented on his name featuring on Lohan's list...

9 James Franco

Another unexpected frequenter of the Lohan bed chamber, James Franco is a respected actor of stage and screen who tends to spend his spare time posting avidly on social media (seriously, check out his Facebook) and studying for a PhD. There are also some questions as to the truth behind Franco’s appearance on Lindsay’s list: Lohan obviously claims the two slept together, while Franco denies it. He claims that Lohan did come onto him while they were both staying at the infamous Chateau Marmont Hotel but that he declined the offer as she “had issues.” Instead he says, they bonded and were just good friends. Franco has since mocked the incident in the 2013 flick This is the End, claiming he and Lohan got it on after she mistook him for actor Jake Gyllenhaal. Jury’s still out on whether anything actually went down (pardon the pun).

8 Ashton Kutcher

Although no rep has confirmed or denied it, rumours have for a long time circulated around Tinseltown stating that Ashton and Lindsay were once a thing. In fact, with the bedroom list now revealed, it seems Ashton’s current squeeze Mila Kunis is not happy with the pair’s friendship and has asked him to cut ties with the former child star. Of course Ashton himself is no stranger to complicated romantic entanglements: when his marriage to Demi Moore broke up, there was what appeared to be a swift route from older to younger brunette on Kutcher’s part. It remains unclear when, if ever, Kutcher and Lohan hooked up.

7 Joaquin Phoenix

Another wild card on the list, Oscar winning actor Joaquin Phoenix hardly seems like Lohan’s type, nor indeed does she seem like his. However the pair were rumoured to have briefly dated in 2006. More interestingly, Phoenix was reportedly spotted in an L.A nightclub with Lindsay and fellow esteemed member of the Lohan bedroom list, Ryan Phillippe, in 2010. It has been suggested that the affair between Phoenix and Lohan was short lived, in particular given the fact that he is listed as “J. Phoenix” on the countdown of bedroom conquests. To be fair to Lindsay, Joaquin is a hard one to spell.

6 Justin Timberlake

This is where the celebrity gossip gets really good: Both Lindsay and Justin Timberlake have been been courting celebrity from an early age through their affiliations with Disney, so it’s likely their paths may have crossed more than once. However, ever since Justin grew out his N’Sync hair he has been linked to Hollywood actress Jessica Biel, rendering any rendezvous will Lohan a little more suspicious. Both Lohan and Timberlake were spotted at a New York club together in 2009, with Lohan tweeting - and later deleting the message - “Where’s jb cheater?” We can only assume JB stands for Jessica Biel…

5 Colin Farrell

Ah everyone’s favourite Irish rogue. These days Colin Farrell may have calmed down somewhat, but when he first appeared on our screens, he came across as quite the party boy. Remember he and Britney hooking up? Well, Lindsay claims she also canoodled with the actor. The two were spotted together around 2004 at several Hollywood parties but were never officially dating. When questioned by E! news for comment, Farrell’s reps said they do not comment on any gossip that is more than 9 years old. Considering the alleged banging went on exactly 10 years ago, that seems convenient.

4 Zac Efron

Another squeaky clean Disney start to mature before our very eyes, Zac Efron is, in many ways, what Lindsay Lohan could have been: an attractive, successful actor who cut their teeth at the Disney studios. Now, as with many on this list there is no hard proof that anything actually went down between the two former teen stars; however, when confronted by the paparazzi about the alleged entanglement Efron appeared a little caught off guard. A glorious set of gifs have since commemorated his discomfort. We’ll let you decide if you think he looks guilty.

3 Adam Levine

Having been voted People magazine’s Sexiest Man Alive for 2013, many people think that Lindsay should count her blessings rather than cry about them on Oprah. One such blessing most definitely is bedding the Maroon 5 frontman - but considering the singer has something of a reputation when it comes to the opposite sex, the rumour is hardly surprising. Levine hasn't commented on the revelations and is currently engaged to Victoria’s Secret model Behati Prinsloo. As the singer was previously reported to have had flings with Jessica Simpson, Paris Hilton, Cameron Diaz, and Natalie Portman among others, it seems quite believable that lucky Lindsay may have got a look in.

2 Orlando Bloom

Another curious contender on the list, British actor Orlando Bloom is listed as “Orli” on the list, suggesting that the two may have been closer than we think. It’s hard to pin down when the alleged incident actually took place, however: although recently divorced, Bloom was of course, for a long time, married to all around babe Miranda Kerr and prior to that was in a relationship with actress Kate Bosworth. Orlando did pretty much explode out of nowhere in the early noughties so it’s quite possible that a more established star such as Lohan had her way with him in the early days.

1 Heath Ledger

Yes the number one spot has to be Heath Ledger. His untimely death in 2008 at the age of 29 means that none of us will ever even have the hopes of experiencing this bedroom conquest. More worryingly however, Ledger’s death may also serve as a warning to the troubled star. When he was found dead at his home, fans and colleagues around the world were shocked but it transpired that a deadly cocktail of prescription drugs sent him to his grave. Lohan’s run ins with the law and substance and alcohol abuse issues have been well documented and it. In the aftermath of Ledger’s death it was reported that he and Lohan were dating, although Ledger’s family have never confirmed this. Either way, Lohan has some serious mountains to climb is she wants to get clean, let alone restart her career.


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