Continuity mistake: In the scene where Dylan is chatting with Jamie, you can see a computer screen right behind her. You can see that a window on the desktop changes position and size between shots, even though no one is using the computer at any time during conversation. (00:54:00)

Friends with Benefits (2011)
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Directed by: Will Gluck
Starring: Mila Kunis, Patricia Clarkson, Justin Timberlake, Jenna Elfman
Genres: Comedy
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Answer: In real life, and since it's restoration in the late 1970s, it is illegal and impossible for anyone to climb and/or sit on the Hollywood sign. It is fenced off and electronically monitored by security 24/7.Unless they found a way to bypass the security, this is movie fiction.
raywest ★
But the question is how they managed to sit on that sign and not how they managed to get in.
As to "how they managed to sit on that sign," in the past, others have climbed and sat on different letters of the sign. Each of the steel corrugated panel letters is attached to vertical steel girder structures, which have multiple horizontal bracing steel beams attached behind the letters. Every individual letter also has 2 to 3 steel ladders behind the steel panels. Jamie and Dylan climbed up to the lower inner part of the second "O," and both of them sat on one of the horizontal steel beams that has a depth of 8 inches, enough room to accommodate them sitting.
Super Grover ★