Brook Benton’s “The Boll Weevil Song.” Uncle Kracker’s “Drift Away,” featuring Dobie Gray, holds the mark for longest run atop the tally, having reigned for 28 weeks in 2003-04.

After scoring a No. 1 hit with Chesney on "When the Sun Goes Down," Uncle Kracker would go on to release "Smile," from his Happy Hour album, in 2009. The song became a multi-platinum hit and ...

Kenny Chesney is well-known for his laid-back beach songs, and he crossed genre lines when he teamed with Uncle Kracker for “When the Sun Goes Down.” Uncle Kracker’s real name is Matthew Shafer, and ...