Matchbox Twenty rose to international fame with their debut album, Yourself or Someone Like You (1996), which was certified 12× Platinum (diamond) in the United States and multi-platinum in Australia, Canada, and New Zealand.

Their second album, Mad Season, released in 2000, charted in the top three on the Billboard 200 and was certified 4× Platinum in the United States.

"Real World" and "Back 2 Good" proved to be the band's first entries into the Billboard Hot 100, after the rule was terminated.

Thomas was supposed to act only as a songwriter for "Smooth", but Carlos Santana had him sing for it after hearing the song's demo.

The video for "Bent" made fun of singer Thomas's increased fame from "Smooth" by showing the other band members assaulting him.

The album again spawned successful singles "Disease" (written with Mick Jagger), "Unwell", and "Bright Lights".

The EP featured previously unreleased live and acoustic versions of songs like "Push" and "If You're Gone", as well as a new track, "Suffer Me".

In 2004, the band released a live DVD, Show: A Night in the Life of Matchbox Twenty, filmed in Atlanta and featuring 20 songs, including all of their previous successful singles.

Before taking a hiatus later that year to allow other members to pursue side projects, such as Paul Doucette's solo band The Break and Repair Method, rhythm guitarist Adam Gaynor officially left the group.

In January 2007, Rob Thomas released a single, "Little Wonders", which he wrote for the Disney movie Meet the Robinsons.

Following Australia, Matchbox Twenty visited the UK for the first time in five years to play six concerts in Cardiff, Wembley, Birmingham, Glasgow, and Manchester.

He stated in an interview to Billboard that he expected that the other members of the band might begin work on Matchbox Twenty's next album without him.

At the Taste of Chicago on July 2, 2010, Thomas said that Matchbox Twenty would be recording in the fall for their fourth studio album.

Rob Thomas posted on Twitter that he was "heading out next week to start writing the new mb20 record" on September 13, 2010.

[9] On April 9, 2016, Kyle Cook left the band citing a communication breakdown between the members, but returned in 2017.

The band played a one-off performance headlining in St. John’s, Newfoundland, Canada for the Churchill Park Music Festival in July 2022.

[17][18][19][20] On June 20, 2022, a video was posted on the band's Twitter account, confirming that a new album is in the works, despite Rob Thomas denying this in interviews the previous year.

In May 2005, nine years after the release of Yourself or Someone Like You, Matchbox Twenty was sued by New York City resident Frank Torres, the man featured on the album's cover.

In legal papers, Torres claims the group "knowingly, intentionally and maliciously" used his picture on the cover, causing him mental anguish.

Matchbox Twenty received a nomination for Best Rock Album twice at the Grammy Awards, for Mad Season in 2001 and More Than You Think You Are during 2004.