Signed to Mercury Records between 1996 and 2003, he released five studio albums for the label – Mark Wills, Wish You Were Here, Permanently, Loving Every Minute, and And the Crowd Goes Wild – as well as a greatest hits package.

Two songs originally recorded by Wills, "Somebody" and "What Hurts the Most", were later hit singles for Reba McEntire, Jo O'Meara, Rascal Flatts, and Cascada respectively.

[2] In his teenaged years, Wills played in garage bands, taking inspiration from rock groups such as Bon Jovi.

[2] Wish You Were Here, Wills's second album, was his most commercially successful, earning a platinum certification from the Recording Industry Association of America.

The lead-off single "I Do (Cherish You)" and its follow-up, "Don't Laugh at Me", both reached number two on the country charts, with the former bringing him to the Billboard Hot 100 for the first time.

Co-written by Bill Anderson, Skip Ewing, and Debbie Moore, it became Wills's first number-one country hit in 1999.

In 2000, he voiced the character of Huckleberry Finn in MGM's animated remake of Tom Sawyer, Wills's only film role to date.

Wills's eighth chart entry was a cover of R&B singer Brian McKnight's 1998 hit single "Back at One".

He did not record again until country singer Clint Black signed him to his Equity Music Group label in 2006.

His first album for the label, titled Familiar Stranger, was originally slated for release in September 2007,[5] and was repeatedly pushed back due to the poor chart performance of "Take It All Out on Me" and "Days of Thunder."

In late 2009, he released then a fifth single, "Crazy White Boy", written by Brett James and Blair Daly.

Wills released the compilation album 2nd Time Around in July 2009, which comprises re-recordings of several Mercury singles.

Wills released a new single in January 2011 called "Looking for America", written by Bernie Nelson, Philip Douglas, and Jeremy Bussey.

He was invited by Vince Gill to become the 218th member of the Grand Ole Opry on December 21, 2018, and was inducted on January 11, 2019[4] In 1996, Wills married his wife, Kelly, whom he met at Atlanta's music club, Buckboard.