The 29-year-old had to do a lot of networking for his role in David Fincher's highly anticipated new movie about the rise of Facebook creator Mark Zuckerberg.
He tried obsessively to land the role of Sean Parker, auditioning continually for Fincher before he eventually got the gig.
Timberlake told Scottish newspaper the Daily Record: 'When I went in, I told them, 'We can read this scene butt naked if you guys want,' I tested more times than anyone else in the film.'
Before Justin had landed the role, he had auditioned so many times already that even real-life Parker knew he was desperate to play him.
The SexyBack singer added: 'He [Parker] seemed very nice, he mentioned that he had read the script and he thought I was playing the part.
'It was awkward to have to say I didn't know yet if I had the job, I certainly wasn't just hammering at that particular door - I was trying to kick it down.'