[Solitaire1]

I'll disregard podcasts and just use the information on the music I own. Also, I'll disregard tracks that start with a punctuation mark.

Sorted by Artist:

First, 101 Strings Orchestra
Last, ZZ Top

Sorted by Song:

First, "1/2" by Cledus "T." Judd
Last, "Zui-Zui-Zukkorobashi" by Yo-Yo-Ma

Sorted by Album:

First, "1" by The Beatles
Last, "You're Pitiful" by "Weird Al" Yankovic

Just for fun I add the following:

Sorted by Length:

Shortest, "Angelus Bells" (9 seconds) by Erich Kunzel & The Cincinnati Pops Orchestra from the album "The Sound Of Music"
Longest, "Ashes Are Burning" (23 minutes and 53 seconds) by Renaissance from the album "Tales Of 1001 Nights - Volume II"