I'd have to stick to artists rather than songs myself (and 10 just isn't enough).
In no particular order, here's a pretty decent approximation of some of my all-time heavy playlist:
* Replacements (Let It Be, Pleased to Meet Me)
* Drive Like Jehu (Drive Like Jehu; Yank Crime)
* My Bloody Valentine (Loveless, various EPs)
* Yo La Tengo (Painful, Electr-O-Pura)
* Unwound (Repetition, Leaves Turn Inside Out)
* Kruder & Dorfmeister (K&D Sessions, DJ Kicks)
* Marisa Monte (Rose & Charcoal)
* Stan Getz (60 years to pick from)
* Frank Sinatra (Songs for Swinging Lovers, A Swingin' Affair)
* James Brown (various)
Though lately I've been listening to either pretty new stuff (Postal Service, And You Will Know Us By The Trail of Dead, Pretty Girls Make Graves, Ambulance LTD, David Holmes) or really old stuff (Dean Martin, Josephine Baker, Peggy Lee, Rufus Thomas, Iggy Pop & the Stooges).