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Swift's Fearless and her self-titled album finished 2008 at number three and number six respectively, with sales of 2.1 and 1.5 million.

Later in October 2006, she released her self-titled debut album, which produced five hit singles on the Billboard Hot Country Songs charts and was certified 3× Multi-Platinum by the RIAA.

The New York Times described Swift as "one of pop's finest songwriters, country’s foremost pragmatist and more in touch with her inner life than most adults".

According to Nielsen Sound Scan, Swift was the biggest selling artist of 2008 in America with combined sales of more than four million albums.

Frank Sinatra, Stevie Wonder, Paul Simon (as performers), Daniel Lanois, Ryan Tedder (as record producers), and Bob Ludwig, Tom Coyne (as mastering engineers) & Tom Elmhirst (as an engineer/mixer) are the biggest winners in this category with three victories each.

Ludwig is the only person to win the award three consecutive years (2013–2015).