As for TV series, I can't say I've watched many, so I've definitely never rewatched any.
However, I get back to old movies and games all the time.
I constantly rewatch movies that, for a reason or another, have left a mark on me such as The Godfather trilogy (mainly the first two) and the Rocky series. Other than that, I love going back to the first Jurassic Park, Apollo 13 and (for some reason even I can't understand) You've got Mail...
I replay games up to the 6th generation all the time, especially stuff for the Master System, Saturn and PS1/PS2. Based on these consoles I've cited, apart from games that are meant to be replayed (like sports, racing and fighting titles), the video games I've cleared over and over again the most times are probably:
Alex Kidd in Miracle World -- Castle of Illusion: Starring Mickey Mouse (Master System)
Princess Crown -- Guardian Heroes (Saturn)
Rockman X4 -- Castlevania: Symphony of the Night (PlayStation)
Ace Combat 5: The Unsung War -- Metal Gear Solid 3: Subsistance (PlayStation 2)
and, my favorite game of all time,
METAL GEAR SOLID