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Anderson continued to record steadily and mounted a major comeback in the early '90s, starting with 1992's Seminole Wind. Its title track went to number two, and the follow-up, "Straight Tequila Night," went all the way to number one; "When It Comes to You" also made the Top Five. Anderson scored another number one in 1993 with "Money in the Bank" and hit the Top Five three times over 1994-1995 with "I Wish I Could Have Been There," "I've Got It Made," and "Bend Until It Breaks." Though he hasn't been back since, Anderson's albums and singles continue to make the lower reaches of the country charts, evidence of a still-solid fan base. What was termed a comeback album of sorts, Easy Money, produced by John Rich of Big & Rich fame, appeared in 2007. Bigger Hands followed in 2009, and he released Goldmine in 2015.
Anderson suffered an undisclosed health problem in the late 2010s, an experience he chronicled on 2020's Years. The album was written in collaboration with Dan Auerbach of the Black Keys; Auerbach also produced Years and released it on his Easy Eye Sound label. ~ Steve Huey