Crossword puzzle clue "raising sand singer who won five grammy awards in 2009 2 wds"

"Raising Sand" singer who won five Grammy Awards in 2009: 2 wds.

"Back to Black" singer who won five Grammy Awards in 2008: 2 wds.

Third baseman who won both the Gold Glove and the Silver Slugger awards in 2009 while on the Washington Nationals: 2 wds.

Best New Artist at the 2009 Grammy Awards

Name on five Rolaids Relief Man Awards, 1999-2009

Lorena who won two 2009 ESPY awards

50 ___ (rapper who won a Grammy with Eminem and Dr. Dre for 2009's "Crack a Bottle")

"9 to 5" singer who won the Willie Nelson Lifetime Achievement Award at the 2016 CMA Awards: 2 wds.