Well I don't think anyone would freak out if I told them I watched the a million times. So here's my top 5 in no particular order

I admit, I don't watch very much anime, and I don't rewatch much either.

Hello Vizzed.
Hello "Brain-Splattered".

...
Why Not?

(1) Lipin the 3rd. (It's Funny.)
(2) Dragonball. (The First One. It's Funny.)
(3) Ghost In The Shell. Stand Alone Complex.
(It makes me ponder Odd "Bladerunner" type stuff.)
(4) Fist Of The North Star. (It's Funny.)
(5) Tekkaman Blade.
(The American T.V. Dubbed Version Was Amazing.)

The Last Entry is a special one. I have no idea why but the stuff the american script writers and actors did brought allot to the table on that show.

Normally I would mention "The Dirty Pair" but the original English Dub can not be found online. The new english dub is crap compared to the first ones on V.H.S.

Another I normally give a shout out to is the "Tank Police". (Again it is Comedy Gold.)
But Finding that stuff is like Finding the Holy Grail or something.

Good Times.
Good Luck On Your Next Project.
Thank You.

Good Luck To All.
Peace.

I'm sure i'm not the only one but sometimes ill re watch an anime for a specific fight or something that happened I wanted to re see but then ill get to those episodes that was ok on the first run but are SO BORING every watch after but some animes arnt like that some examples are:

Highschool of the Dead

Wolfs Rain

Darker then Black 

Phantom Requiem For the Phantom

Clannad

My top 5 to rewatch would probably be...

1. Durarara!!
2. Death Note
3. Eureka 7
4. Samurai 7
5. Naruto+Shippuden (Yeah, I marathon that s***)

I enjoy rewatching anime, it gives me more to do.

#5 Elfen Lied. Still not sure how to pronounce Lied...
#4 Bleach. Kick butt series.
#3 Naruto and Naruto Shippuden. Amazing!
#2 Shiki. Really messed up.
#1 Sword Art Online. Best anime I have ever seen!

I enjoy re-watching anime in my free time, as well as starting new ones. Here are some of the ones I am currently re-watching:

#5 Attack on titan- It's just a good anime in my opinion
#4 Fate Stay Night- I watched it for the first time about two weeks ago, I liked it so much, I'm watching it again
#3 Death note- Great anime
#2 Sword Art Online- I instantly liked this anime when I started watching it. Can't wait for the next season!
#1 Naruto Shippuden- Probably my favorite anime, there's a lot of filler, but I still enjoy it. This is great for re-watching since there's around 600+ episodes. 

The only anime I have ever re watched was Naruto. I have re watched the first part a few times, and am currently working on it again. 

There are a ton of animes that i would watch over again and one of them is my childhood anime Inuyasha I just love that series and it never gets old I can always watch all of its fights and be as surprised as always.

I can always watch sora no otoshimono as well because I never get tired of all the comedy that is implanted into that show. I also love the angels' personality and the protagonists pervy attitude.

Toradora! is one of my favorite romances because it is a perfect mix of both a comedy, school life as well as a romance and I love the drama and the realsm that is added into the series. There are a lot of funny personalities in that show and I never get tired of getting to know them all over again.

Horizon in the Middle of Nowhere is one of those animes that you would expect would be completely random but that ends up being really interesting. I love the plot, all of the fights, and the soundtracks as well. It makes me wish that the world was as modern as it is over in the series. 

The Pet Girl Sakurasou just because of Mashiro. Love her.

No Game No Life because it is an intriguing series that amazes me as a gamer.

legacyme3 : Awesome, I had no idea you liked that s*** xD ( Naruto)

------

I have watched a lot of anime but the ones I would re-watch is:

1) Black Bullet
I almost like all the characters in here. My favorite being Tina Sprout.

2) Star Driver
Takuto's transformation is fabulous ! Also, the music in here is pretty darn epic.
https://youtu.be/0AFw9pVg1SY

3) Naruto/ Naruto Shippuden
I hate Sasuke ... but still cool at times.

4) Lovely Complex aka Love*Com
One of my favorite romance anime's

5) Attack on Titan
Interesting story and great animation

I watched numerous anime over again such as Dragon ball z or naruto.

I only have 3 anime that I'm just constantly watching over and over again. They're just so good to watch that I don't really have any time to watch any of the other ones. I will list them in order of my favorites:

1. Claymore - just an awesome anime to watch, in my opinion. I like everything about it...the music, the action, the graphics. Its just really all well done. This show only lasts for 30-something episodes but its the one I watch the most.

2. Dragon Ball Z - this is actually arguably my favorite anime of all time. I just don't watch it as much as I do Claymore, so I'm more inclined to like that one better. But I've definitely been watching DBZ for the longest...no question about that.

3. InuYasha - I actually don't really watch this too much anymore. I'll watch it on occasion, and I still love what goes on in this show. I especially like the final season they made. It has a cute ending to it

Sailor moon
card captors
ultimate muscle
one piece old school
pokemon
inuyasha
fruits basket

Are the ones I tend to rewatch over and over again without shame. My brother and sister keeps on asking why do you keep rewatching things? And I say well why not? Its better than what's on today, plus its what I want tot do  

I don't really have any particular order, but these are the animes I've watched and re-watched the most.

Outlaw Star

   I've seen it so many times, I can tell what number the episode is, and the title, from, like, the first two seconds of the opening. My friend's didn't believe me. So they tested me, and I passed. XD.

Cowboy Bebop

   Pretty much the same as Outlaw Star (In the way that I can tell you the episode name, not number, in a few seconds.)

Gungrave

   It's just such a sad and action packed anime, one of my top favorites, even though I've yet to meet anyone else who even knows of it.

Soul Hunter

   An older anime, but one of my favorites. There are times it gets pretty philosophical, and the main character Taikobou is just a great character.

The Twelve Kingdoms

   I love everything about this anime, the books are much better, in my opinion, but the anime still moves me to tears. How the world is very different, but so expertly created, it blows me away. It's a great watch, and read.

   I haven't mentioned any Gundams or .Hacks//, but this list could go on for much, much longer. But, you said top 5.

My List would have to be...
1.) Cowboy Bebop (Possibly the best anime ever.)
2.) Fist Of The North Star (Favorite 80's anime movie, sorry Akira...)
3.) Trigun (Between the action and comedy this is a must.)
4.) Kill Me Baby (It's cute, funny, and people might freak a lil that I like it.)
5.) Golgo 13 (He's like Japan's 007, but he works for himself.)

I watch a bunch of Toonami's old animes like Tenchi Muyo,
and DBZ from time to time as well, but since I had to choose... lol

Mine in no particular order are the following:
Death Note
Vampire Hunter D
Ayashi no Ceres (probably #1)
Azumanga Daioh
Cowboy Bebop
Ghost in the Shell (the movie)

Probably some others I've seen over and over...

I don't rewatch anime after I see them the first time... but I will admit that I watch Hellsing Ultimate episodes and Abridged (this one almost monthly).