Vince Gill duet "My Kind of Woman/My Kind of Man" were issued as singles. Loveless and Gill had worked together on a number of occasions prior to this song; notably, she sang backing vocals on his singles "When I Call Your Name", "Pocket Full of Gold", and "Go Rest High on That Mountain". "My Kind of Woman/My Kind of Man" won both artists the Country Music Association award for Vocal Event of the Year. Remz praised the consistency of the previously released singles, but considered "Can't Get Enough" inferior by comparison. Classics was certified gold in 2002. Loveless took a brief recording hiatus at the end of the decade due to her contracting pneumonia and Gordy requiring emergency surgery for pancreatitis. One exception to this hiatus came in late 1999, when she provided backing vocals on Tim McGraw's number-one single "Please Remember Me". 2000–2005: Transition to bluegrass and final years with Epic Loveless returned in 2000 with the studio project Strong Heart. On recording the album, she said she wanted to find songs that appealed to young adults. Steve Earle contributed a harmonica part on the track "You're So Cool". It spawned two top-20 country singles with "That's the Kind of Mood I'm In" and "The Last Thing on My Mind". Despite these chart entries, the album was commercially unsuccessful, with Steve Huey of AllMusic attributing its failure to a more country pop sound than the preceding albums. Alanna Nash shared a similar opinion in a review for Entertainment Weekly, although she praised the track "My Heart Will Never Pass This Way Again" for the inclusion of fiddle music. Country Standard Time reviewer Eli Messinger was more mixed toward the project, considering it inferior to Long Stretch of Lonesome while noting the inclusion of Jimmy Hall and Travis Tritt on various tracks. She released a pair of bluegrass albums between 2001 and 2002. The first of these was Mountain Soul, which consisted of original content and cover songs. Loveless said she had wanted to do an acoustic bluegrass album since 1992 when she met Ralph Stanley. Epic Records executives agreed to let her release the project after noticing positive fan reactions whenever she sang bluegrass songs in concert. Another factor in this decision was the contemporary success of bluegrass-influenced albums such as the soundtrack of O Brother, Where Art Thou? and the works of Nickel Creek. The album included guest