Longest I went was 5 days(somewhat drug induced), and then not much sleep for a couple days after...it certainly did get weird, and just got used by people I was hanging around.

But yeah if you're prescribed sleep meds those can certainly be helpful if you can't sleep, I am prescribed trazodone and 100mg of that will usually knock me out a while, kinda has a weird drowsy feeling in the morning, but I have coffee I can make so that helps that.

Not so sure what the longest someone can go without sleep is though. a lot of times I just barely get any sleep but still lay down and maybe get a couple hours which isn't very effective, and sometimes aside from the time I've mentioned I've gone a couple days with no sleep....haven't been up 5 days aside from that one time.