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 ...

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.