Like many of my age, my first exposure to Herbie was with his groundbreaking song RockIt. I don't mean to minimize the importance of RockIt (which won Grammies and spawned a generation of break dancers and music that used technology in new ways), but that was a brief phase in Herbie's amazing career.
The Miles Davis Years: So What
My main MO for finding great jazz musicians is to start with Miles Davis and work my way out. He played with amazing people who went on to have stellar careers. Herbie's work with Miles was a great beginning.
Post-Davis Bop (Maiden Voyage and Empyrean Isles): Cantaloupe Island
These two albums are musts for anyone who wants to dip their toe in the jazz river. The hook in Cantaloupe Island is tremendous.
Headhunters is accessible, funky, and fun.
(relatively) Modern Work
Rockit (love the video)
Herbie has done a ton of work since the 80's, so I have lots of work to do catching up with him.