The very first song I learned on guitar was Cream's "Outside Woman Blues" - that's not a typical first tune (the opening chord is E7#9), but I liked it, so I learned it.
Stuff in the middle was driven by my fairly eclectic musical tastes (old blues like "St. James Infirmary", standards like "All of Me", jazz like "Take Five", some bluegrass, TV theme songs, etc.) and things I played in various bands - mostly 70s and 80s rock by Zeppelin, Skynyrd, and so on, and more folky acoustic stuff by CSNY, Cat Stevens, Dan Fogelberg, John Prine, etc. for solo gigs and acoustic groups.
At the moment, I'm working with a band doing rock/pop/jazz from the 50s-now, and the tunes we've added so far this month are:
Me & Julio - Paul Simon
Peggy Sue - Buddy Holly
What I Like About You - The Romantics
Feeling Alright - the version by Joe Cocker (tune by Dave Mason)
Use Me - my own jazzy arrangment of the Bill Withers tune that was recently covered by Uncle Kracker
Yesterday - The Beatles... I'm trying to work out a way to cover the string parts on the album so we can get as close as possible to the original
La Bamba - the original by Ritchie Valens (work those tremolo chops!)
Roadhouse Blues - the Doors
If you work much with cover bands, you'll find yourself constantly learning new songs. I've probably learned somewhere around 3500-4000 different songs (so far), although at any given moment I can probably only play 300 or so without music... of the 8 tunes my band added this month, I've done 4 with other bands, so you do a lot of relearning - which goes really fast. Also, the more you get used to learning tunes, the better your ear gets, and the faster you get new ones down - learning Peggy Sue was a breeze, because I'd heard those three chords a million times already (ok, four if you count the bridge), and the lead break is chord based.
Then there's the stuff I work on to make myself a better guitarist. In the past month, I've been doing these:
My Favorite Things - the Wes Montgomery version (cool octave melody, nice jazzy break)
Suite for Lute - Philipp Franz Le Sage de Richee
Grand Sonata, op.22 - Fernando Sor (got a lot of work left to do on that one)
As Time Goes By - a gutiar arrangement I found by Stan Ayeroff
I'm also working on learning the lead for Everlast/Santana's "Put Your Lights On" so I can do that with the band, and the other day I was driving along listening to the radio, and I heard John Mayer's tune "Daughters", and thought I'd like to learn that one. It'd make a good solo acoustic tune.
I wouldn't stress much over where you are compared to others... the more you learn, the more you'll know, and the more you know, the faster you'll learn.
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