Answer
Dwight Yoakam has had two number-one singles on the Hot Country Songs chart: "Guitars, Cadillacs, Suitcases, and Boots" in 1990 and "I'll Be Your Love Tonight" in 1992. He has also had six other singles reach the top ten, including "Honky Tonk Man" (1986), "Little Sister" (1987), "Streets of Bakersfield" (1988), "Ain't That Lonely Yet" (1989), and "Fast As You" (1993).