Before he was singing duets with Alanis Morissette and writing hits for Tim McGraw, Ryan Adams came into his own with Heartbreaker, a stunning solo debut. Having just dissolved Whiskeytown, he stuck to his alt country guns but discovered a talent for writing sad, winsome songs like "Come Pick Me Up" and "Sweet Lil' Gal (23rd/1st)." "My Winding Wheel" is a standout.