From A to Z, your first and last iPod song

Ain’t Goin’ Down (Til the Sun Comes Up) - Garth Brooks
Your Man - Josh Turner

“ABC” by the Jackson 5
“You’ve Lost that Loving Feeling” by the Righteous Brothers
“$20 Sack Pyramid” (a skit on Dr. Dre’s Chronic album)

First: ABC - The Jackson Five
Last: Your Mama Don’t Dance - Loggins & Messina
Last numerically: 500 Miles - The Kingston Trio

First: “Aa-Shuu Dekei-oo” by Huun-Huur-Tu (Tuvan throatsinging).
Last: “Zweb,” which is the nickname of someone I interviewed for a project I’m working on.
Last including numbers: “9-9” by R.E.M.

A-Punk by Vampire Weekend (third in this thread!)
Zoot Suit Riot by Cherry Poppin’ Daddies

Numerically, by actual song titles (vs. picking up track #s)
1-900 L.L. Cool J by LL Cool J
99.9f by Suzanne Vega

Not an ipod, but…

About to Begin - Robin Trower
Zombie Woof - Frank Zappa

Non-alpha
#9 Dream - John Lennon
6060842 - B-52s

‘A’ Bomb in Wardour Street - The Jam
Zipper in My Spine - Robyn Hitchcock

Numerical:

12XU - Wire
3000 - Dr. Octagon

For letters:

A.F.U. By Van Halen is first.

Zzyzx Road by Stone Sour is last.

For numbers:

-1 by Mudvayne is first.

742617000027 by Slipknot

Letters:

Abysyian goat toast - The Tailgators

You wont make a fool out of me - Flogging Molly
Numbers:

1985 - Bowling For Soup

88 lines about 44 women - The Nails

A-Tisket, A-Tasket by Ella Fitzgerald comes before Aaron Harris Blues by Jelly Roll Morton.
Last: Zydeco Gris-Gris by Beausoleil. Last with numbers, 1984 Blues by the Austin Lounge Lizards.

Africa by Karl Wolf, a loose remake of the Toto song

Zombie by The Cranberries

99 Luftballons by Nena, if numbers are included

A coral room (Kate Bush)
Zombie (Cranberries)

if A … does not count:
Adia (Sarah McLachlan)

“A-Tisket, A-Tasket” - Ella Fitzgerald (followed by the Steve Miller Band’s “Abracadabra” and George Carlin talking about Abortion)
“Zat You, Santa Claus?” - Louis Armstrong
“99 Luftballons” - Nena

Amen! The only repeats I’ve noted are “Abacab,” “ABC,” “A-Tisket, A-Tasket,” “99 Luftballons” and “500 Miles.”

A-Punk, Vampire Weekend
Your Lucky Day in Hell, Eels

A-Rab by The Sonics
Zorba the Greek by Herb Albert (I feel so unoriginal…)

“A-Punk” by Vampire Weekend was mentioned three times(as susan_foster noted) when you posted and at least once since.

About a Girl - Nirvana
You’re Breaking my Heart - Harry Nilsson

Joe

Thanks for the catch. And now “Zorba the Greek.”

The Accident (Things Could Be Worse) - John Prine
9th & Hennepin - Tom Waits