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Jakob Dylan and his band the Wallflowers were so dreamy and talented, but unfortunately we haven't seen much of them again after they won two Grammys in 2008.
System of a Down had a big hard-rock moment at the turn of the millennium, and won some Grammys for their work.
Shelby Lynne had a successful career for years in country before winning Best New Artist in 2001... and then promptly going back underground in the country world.
Esperanza Spalding won the Best New Artist Grammy in 2011, which was remarkable mostly for whom she beat out: Justin Bieber, Drake, Mumford and Sons, and Florence + the Machine.
Shawn Colvin's "Sunny Came Home" was everywhere in 1997, and it scored her Grammys for Record of the Year and Song of the Year. Shawn, come home and sing for us again!
Remember Los Lonely Boys? Neither does anyone else. But they took home the Grammy for best pop performance by a group in 2005.
Estelle had such potential! Her song "American Boy" was an adorable collaboration with Kanye West, and it got her a Grammy in 2008.
Duffy was part of the Amy Winehouse school of old-school lady singing in the mid 00s. She won Best Pop Vocal Album in 2009.
Dirty Vegas sang "Days Go By" in that haunting car commercial and won a Grammy for their efforts in 2003.