What would you recommend a guy to watch for a 9/11 doc if you had to pick one or two?
First off, if you're only going to consume one thing on OKC, it should be Free Mind Films', A Noble Lie: Oklahoma City 1995 (this second link is not from the film makers and will likely disappear at some point). Scott Horton of The Libertarian Institute and Antiwar.com probably has the best database of OKC interviews and writings but for a one-stop, I recommend the aforementioned.
Regards to 9/11/01, I haven't actually seen a lot of documentaries. It's nearly impossible to produce a documentary of value that doesn't simply focus on one aspect.
I've done quite a bit of reading (often from the sources provided from what I've listened to or watched) and a whole lot more listening for most of my information.
Michael Ruppert's, "Crossing the Rubicon" was an early entry for me.
Daniel Hopsicker's, Welcome To Terrorland: Mohammed Atta & The 9/11 Coverup in Florida is a great one to learn about the fuckery around the security state connected flight school where the alleged pilots learned to fly. It also lays serious doubt on the "fundamentalist Muslims" storyline (important aspect of the official narrative) as it describes their use of cocaine and strippers. Hopsicker's journalism, though requiring some getting used to, has been quite good on 9/11 - though he and I certainly depart on some issues. His overall work on the drugs and arms trade is well worth the visit if that's your thing. His docs and website aren't the most polished, to say the least, but the info is sound and he has several worth the time (I also recommend The Secret Heartbeat of America about the CIA and drugs and In Search of American Drug Lords about, well, the CIA and the mob).
I honestly can't even think of another documentary to recommend. The 9/11/01 whistleblower, Richard Andrew Grove's, 9/11 Synchronicity "podcast" blew my mind when I first heard it. That was around '06 so a lot of info has come to light since then. Much of that info has also come through his subsequent work at the Peace Revolution Podcast. If deep, forensic history is your thing, I can't recommend his work enough (9/11 itself is an infanitesimal portion of his output which is currently under the Grand Theft World podcast).
James Corbett has good 9/11 work though his stuff is getting harder to find online. I would just type "9/11" into his search bar. If you want some pretty easy watching, his 9/11 Suspects documentary is good. It's just over an hour.
Tom Secker's series (I'd also pop "9/11" into his search bar), An Alternative History of Al Qaeda is outstanding. Among other things, it destroys the narrative that western intelligence couldn't have foreseen 9/11/01 happening. Either because it was a novel idea or that they couldn't infiltrate the group. There was plenty of intelligence inside Al Qaeda. These things though not very sexy are integral to the official narrative. If you remove the narrative foundation, what's left?
In fact, as I'm writing this, if you only listen to one podcast from Secker's series, listen to Episode 114 on Ali Mohamed (there aren't 114 episodes in that series btw. He has other content) and then get back to me with your thoughts on the "official story".
Christ, that's enough. If you're interested, you'll pursue it. Have fun.