Today is a natural twofer: Spin Doctors and Blues Traveler. Chris Barron and John Popper went to high school together in Princeton, NJ. They were both in a band called Trucking Company, which turned into Spin Doctors, with Popper going out on his own. But they toured together and created the H.O.R.D.E. festival.
Blues Traveler got recognition first, with their self-titled debut album. It showcased Popper's amazing singing, songwriting, and (in-particular) harmonica-playing talents. His playing is like nothing we've heard before, and likewise, the musical style of the band is not like anything else going on in 1990.
This is the best sounding live performance I can find of this great song
Blues Traveler – But Anyway (live)
I bought their follow-up album, Travelers and Thieves, which got radio airplay with All in the Groove. But it was otherwise more of a longform jam album. The next album didn't do very well, but the one after that, 1994's Four, contained their biggest hit songs, including Run-Around, and this favorite - which is really a big F-You to the hit radio industry
An interesting video all-around
Blues Traveler – Hook (live at Howard Stern Birthday Show)
Their next release had some good stuff, but didn't really chart.
Spin Doctors are a One-Album-Wonder. In 1990, they produced Pocket Full of Kryptonite, which got released in '91, and stayed on the radio through '93. In addition to What Time Is It?, the album contained these mega-hits
I had totally forgotten that Dennis Miller had a show
Spin Doctors - Little Miss Can’t Be Wrong & Jimmy Olsen’s Blues (live on Dennis Miller)
Spin Doctors - Two Princes
Their next album, released in '94, had some minor hits, but if you look at their live performances that year, Chris Barron is clearly messed-up, which led to their demise. Plus the lyrics to their hits didn't do well over time.