The movie is actually called Loser (starring Jason Biggs) from 2000 and Wheatus had a major hit with the song 'Teenage Dirtbag' :-)
This is the soundtrack (according to IMDB):
"Don't Fight It Baby"
Written by Wayne Hector, Steve Mac and Alistair Tennant (as Ali Tennant)
Performed by Five
Courtesy of BMG Records (UK) Ltd./Arista Records, Inc.
"Teenage Dirtbag"
Written by Brendan B. Brown
Performed by Wheatus
Courtesy of Columbia Records
By Arrangement with Sony Music Licensing
"Freakin' You"
Written by Alex Gifford, Nathaniel Hall and Michael Small
Performed by Jungle Brothers
Courtesy of Gee Street/V2 Records, Inc.
"Boom"
Written by Johnny Douglas
Performed by Trinket
Courtesy of The RCA Records Label of BMG Entertainment
"Pretty Fly (For A White Guy)"
Written and Performed by The Offspring
Courtesy of Columbia Records
By Arrangement with Sony Music Licensing
"Blue (Da Ba Dee)"
Written by Maurizio Lobina, Gianfranco Randone and Massimo Gabutti
Performed by Eiffel 65
Courtesy of Republic/Universal Records
Under license from Universal Music Enterprises
Courtesy of Bliss Corporation
Courtesy of Warner UK Strategic Marketing/BlissCo s.r.l.
Courtesy of BMG Berlin Musik GmbH/Logic Records
Under license from Bliss Corporation and Courtesy of Polydor K.K.
Under license from Bliss Corporation
"Get Down Tonight"
Written by Harry Wayne Casey and Richard Finch
Performed by KC & The Sunshine Band
Courtesy of Rhino Entertainment Company
By Arrangement with Warner Special Products
"Sucks To Be You"
Written by Jason Levine, James McCollum and Anna Goodman
Performed by Prozzäk (as Prozzak)
Courtesy of Epic Records
By Arrangement with Sony Music Licensing
"Out Of My Head"
Written by Tony Scalzo
Performed by Fastball
Courtesy of Hollywood Records
"Brandy (You're A Fine Girl)"
Written by Elliot Lurie
Performed by Erica Lively Orchestra
Courtesy of Muzak
By Arrangement with Network Music
"Go On"
Written by Davide Riva, Alfredo Pignagnoli, Stefano Gambarelli, Donella Galli, Paul Sears and Annerley Gordon
Performed by J.K.
Courtesy of Energy Productions SrL
"What's My Age Again?"
Written by Thomas DeLonge (as Tom De Longe) and Mark Hoppus
Performed by Blink 182
Courtesy of MCA Records
Under license from Universal Music Enterprises
"Stop The Rock"
Written by Noko, Ian Hoxley, Trevor Gray and Howard Gray
Performed by Apollo 440 (as Apollo Four Forty)
Courtesy of Epic Records/550 Music
By Arrangement with Sony Music Licensing
"Right Now"
Written by Mitch Allan Scherr and Butch Walker
Performed by SR-71
Courtesy of The RCA Records Label of BMG Entertainment
"Magna *** Nada"
Written by Jimmy Pop (as Jimmy Pop Ali)
Performed by Bloodhound Gang (as The Bloodhound Gang)
Courtesy of Republic/Geffen Records
Under license from Universal Music Enterprises
"Man Of The World"
Written by Peter Green (as Peter Alan Green)
(heard at Paul's, right after the hospital scene before Chris shows up)
"So Much For The Afterglow"
Written by Art Alexakis / Everclear
Performed by Everclear
Courtesy of Capitol Records
Under license from EMI-Capitol Music Special Markets
"Welcome To The Working Week"
Written and Performed by Elvis Costello
Courtesy of Demon Records, a division of the Demon Music Group Ltd.
"I Will Buy You A New Life"
Written by Art Alexakis / Everclear
Performed by Everclear
Courtesy of Capitol Records
Under license from EMI-Capitol Music Special Markets
"Cabaret"
Written by John Kander and Fred Ebb
Performed by Cabaret-Broadway Cast
Vocals by Natasha Richardson with Alan Cumming
Courtesy of RCA Records
Under license from BMG Special Products
"Aurora"
Written by David Grohl (as Dave Grohl), Taylor Hawkins and Nate Mendel
Performed by Foo Fighters
Courtesy of Roswell Records, Inc./The RCA Records Label of BMG Entertainment
"Mint Car"
Written by Robert Smith, Simon Gallup, Roger O'Donnell, Perry Bamonte and Jason Cooper
Performed by The Cure
Courtesy of Elektra Entertainment Group
By Arrangement with Warner Special Products and Courtesy of Fiction Records Limited/Polydor UK Limited
Under license from Universal Music Enterprises
"The Best Things in Life Are Free"
Written by Ray Henderson, Lew Brown and Buddy G. DeSylva (as B.G. DeSylva)
"Scarborough Fair/Canticle"
Written by Paul Simon and Art Garfunkel
Performed by Simon & Garfunkel (as Simon and Garfunkel)
Courtesy of Columbia Records
By Arrangement with Sony Music Licensing
"Sonata in C Major, K.545 (Andante)"
Composed by Wolfgang Amadeus Mozart
Performed by Jenõ Jandó (as Jenö Jandó)
Courtesy of Naxos of America
"Dance To The Underground"
Written by Anthony Roman, Tommy Williams and Greg Collins
Performed by Radio 4 (as Radio4)
Courtesy of Radio4
"Bad Touch"
Written by Jimmy Pop (as Jimmy Pop Ali)
Performed by Bloodhound Gang (as The Bloodhound Gang)
Courtesy of Republic/Geffen Records
Under license from Universa