Living and performing in the Southern California lifestyle, the boys of Slightly Stoopid found success in their Oceanside, San Diego home and other surrounding cities. Growing up together, Miles Doughty and Kyle McDonald caught the attention of Sublime vocalist Bradley Nowell while still in high school and immediately signed with Nowell's own Skunk Records label in 1995. The boys, who both perform on guitar and bass and sing for the group, released two albums with the Skunk Label. Their self-titled debut album appeared in 1996, and the reggae heavy sophomore effort, Longest Barrel Ride, dropped in 1999. Though their distribution remained primarily in Southern California, their debut album is now a hot commodity as it is no longer in print.

The boys have the quintessential relationship - growing up together in one of California's premier surf towns, the boys have learned to perfect the modern pop sound that represents the California lifestyle, much like so many other popular groups today like Jack Johnson, Red Hot Chili Peppers and Sublime. After several years of touring and delivering more of reggae sound, the boys performed an hour-long set broadcast on San Diego's Clear Channel Rock 105.3. The 2001 performance, which occurred just a week after Jack Johnson did the same thing, gave the boys big time exposure in their little So-Cal bubble and prompted the band to release the album Live and Direct - Acoustic Roots. The performance was recorded with their own "Stoopid Records" imprint and had fans screaming for more stoopid material. The album sold almost 20,000 copies and was a fan favorite.

Over the years, the group has toured with Blink-182, the Marley Brothers, G. Love & Special Sauce, Pennywise and more. Their album Closer to the Sun made the Billboard Top 200 at its debut, and they released a live album in 2006.