802. This Land Is Your Land by Woody Guthrie (1944)

Guthrie got sick of hearing Kate Smith's version of Irving Berlin's "God Bless America" on the radio. He felt the song disingenuous and decided to write a song he felt better reflected America. Guthrie sometimes changed the verses based on his mood. Some of the lyrics were overtly leftist and he modified them as he felt appropriate. Over time, the song has lost its overt political connotations.

http://www.youtube.com/watch?v=wxiMrvDbq3s

Kate Smith's "God Bless America":

http://www.youtube.com/watch?v=pCavKL2zdjM

982. Steppin' Out With My Baby by Tony Bennett (1993)

Tony Bennett experienced an amazing comeback after releasing this Irving Berlin standard. Gen X loved it and he ended up on MTV Unplugged in 1994. The original version appeared in the 1948 movie Eastern Parade starring Fred Astaire. 

Best Line: If I seem to scintillate

It's because I've got a date

http://www.youtube.com/watch?v=St0HZCdPVx8