I love making Top 5 Lists :) This list is of the Top 5 Mot Re-Read Comics in my collection. Are they the BEST comics? No. Are they the most expensive? Again, no. These are jut the five comics that I could, can, and do read over and over and over again. Not Trade Paperback Collections, not Graphic Novels, but individual comics.
You should make a list like this, too :)
NUMBER FIVE

HEMBECK 1980 #2 (FantaCo Press) - Fred Hembeck was one of my biggest inspirations to become a Comics Nerd back in the day, and this was the first independent press comic I ever bought. Fred's voice is that of the every-fan circa 1980, and he educated me through his comic strips about the history and depth of comics and comics fandom with each and every page.
NUMBER FOUR
ATARI FORCE #1 - I actually started this series with issue #4 and then had to track down the first three issues via mail order back in the day, and this is the issue that my Brother and his Girlfriend (now wife of over 20 years) got for me their first Christmas together with us. This issue sets in to motion the greatest sci-fi epic story I have ever read in comics, and I'm surprised it hasn't gotten a major collector edition hardback yet considering that it's only 20 issues long (21 if you count the stand-alone "Atari Force Special").
NUMBER THREE

PACIFIC PRESENTS #1 - I originally picked this up for the Steve Ditko "Missing Man" feature (which was "Meh"), but The Rocketeer was the part I ended up falling in love with! And such perfect timing, too... followed The Rocketeer through all the comics, up to and including the Summer of 1991 when I got to meet Dave Stevens and see an early screening of The Rocketeer in a very nice theater! The storie in thi comic always remind me of that magical "There's more to comics than Marvel & DC" time of my life :)
NUMBER TWO

WHAT IF #44 - "What If Captain America Were Revived Today?" imagined a Marvel Universe where the frozen body of Captain America wasn't discovered till the 1980's - Meanwhile, some unknown "patriot" unleashed some imperfect clones of Cap and Bucky, who turned America in to something more akin to Nazi Germany than America. This was my first taste of a comic book being overtly political, and th REAL Captain America's speech at the end always makes me emotional.
NUMBER ONE

SUPERMAN ANNUAL #11 - "For The Man Who Has Everything", Alan Moore's greatest Superman story ever (and he wrote A LOT of the greatest Superman stories ever). This was written in such an incredible way, allowing the reader to piece it all together just as fast as the author wanted us to piece it together... it's just a beautiful and moving story :)