I stopped buying videos years ago due to streaming but below are my favorite purchases of all time...
One video that comes to mind is Kids In Emerica. Roxy Music+Tosh at his peak+Heath/Herman/Spanky/Leo+Reynolds in a leather jacket=Nostalgia for me. The cherry on top was the secret menu.
Other draft picks are:
-Video Radio (Transworld, the trip that made Jamie Thomas put Cole on Zero)
-Sight Unseen (Transworld, Henry fucking Sanchez)
-Sorry (duh)