But after several hiatuses, and a solo career for lead singer Rob Thomas - including providing the vocals on Carlos Santana's global smash, Smooth - their popularity waned.
Yet things seem to be looking up for the band again; their most recent album, North, released late last year, debuted at number one on the US Billboard charts. This album brought Thomas and the band to play in Hong Kong for the first time on Monday, as part of their more-than-60-date world tour.
They kicked off the show at Star Hall, in Kowloon Bay, with Parade, a track from the new album, then moved on to 2000's Bent. It caught me off-guard that they'd play one of their most well-known songs so early in the show, but the crowd certainly wasn't complaining as they loudly sang along.
Thomas joked that they planned to be the house band for the night, and would keep on playing until they were kicked out.
MB20 certainly delivered, with an energetic, enjoyable set. The charismatic Thomas, with that distinctive, trademark twang to his vocals, and guitarist Paul Doucette - who deserves his own shout-out - dominated proceedings with their powerful onstage chemistry; Doucette's inspired playing was a joy to watch.
The noise from the audience grew steadily as the set list continued, especially with the playing of classics such as Real World and If You're Gone.
After slowing things down with I Will - which started with a single acoustic guitar - they moved neatly into Unwell, which had the crowd swaying, and joining in enthusiastically (if not always in tune).
Then they upped the tempo with the rocking Radio. Several songs later, the show came to an end with a three-song encore.
Given the crowd's modest size, it's easy to forget that Matchbox Twenty were once a household name.
Yet the intimate setting made the show feel like a no-nonsense gig for an up-and-coming band, who care only about playing real rock and roll. And there's absolutely nothing wrong with that.