Expanding the Repertoire

I knew this day would come eventually. General rule of thumb that one of Berklee professors told my class was that ANY artist seeking to have a solid repertoire and grasp of classic songwriting should have 250 songs in the bag. I do not have 250 songs. Probably about 45 (and that's counting originals). They have gotten me to this point in my career, but its not cutting it anymore. It's time to add some more variety. So what songs am I going to be getting under my fingers?
Here are some that I am really looking forward to learning:

The Beatles:
All You Need is Love, Blackbird

Springsteen:
Dancing in the Dark, Im on Fire

Sublime:
What I Got

Norah Jones:
Sunrise

Sara Bareillis:
Love Song

U2:
Still Haven't Found What I'm Looking For, With or Without You

Matchbox 20:
3A.M.

Sheryl Crow:
All I Wanna do is Have Some Fun, Favorite Mistake

Lucinda Williams:
Car Wheels on a Gravel Road

Paula Abdul:
Straight Up

Regina Spektor:
Fidelity

This will be one whole other set worth of music....but I have about 20 more full sets to learn! So what am I going to learn? Tell me! Leave a comment and let me know what songs you would like to cover! Tell me what you think of the covers I listed, too!

Dylan