I'm not entirely sure what my last actual video store rental transaction would have been.
The last peak time for me renting movies though, was in college. For the first couple years, I lived in a dorm on campus that was only a couple blocks or so from down town main street. I don't think there were major chain rental places right down there, but we did have Mike's Movies and Music, which (if memory serves) rented most of their VHS tapes for 49 cents a night. New releases, DVD, and maybe some stuff like anime was structured (and priced) more like the typical rental places, but the older stuff was a great deal if you were just picking up something to watch that night, and returning it the next day.
Similarly, the first summer I was in town (well, half the summer) and subletting an apartment, we were up the street from Video Update, which had a deal on renting something like 3 or 5 (older) tapes at a time. So between that, and spending as little on food/etc as we could, there were plenty of nights spent watching movies with the windows and doors open in lieu of running the AC, eating the finest cheap hot dogs, etc.
Between those, I "caught up" with a ton of movies with friends and roommates. On, at best, a 20" TV. - first year I was literally using a 13" Apple color monitor and computer speakers.
The latter half of college was when I stopped going to rent movies as much. A lot of the smaller stores like that got hit early by a massive drop in revenue due to Napster and file sharing, and shifted strategies or closed. At the same time though, DVD had been out long enough to be more ubiquitous, but lacked the bargain rental pricing. It started to make more sense to just peruse the $5 DVD bins at Wal Mart than spending a few dollars to rent a movie. Or I was just buying new releases. Heading to the rental place became less common as our collections grew. I do remember going to rent a few anime titles though, before getting into that.
Years later, Netflix by mail really got me back to that early college feeling for movies. Filled up the queue with a variety of meant-to-watches, classics, looked interesting, etc titles. I ended up cancelling the disc part just 'cause I wasn't watching as many movies, but it was still great while I had it. Was very rare for me to get a disc that didn't work.
Honestly, never really got that much into renting games. We were usually subject to some restriction on playing, so outside of a few times during summer vacation, usually we weren't going be able to get our money's worth from a few days with a game. Last one I remember actually renting was
Mario Kart, which we ended up buying a copy of later.
GI Joe for NES was another than I really recall.
Otherwise, I remember folks scoring a lot of deals on games when rental stores cleared them out, but I wasn't one of them
