Johnny Winter
Winter had been rocking since he was fifteen years old but wasn't signed to Columbia Records until 1968. His advance - $600,000 - was the largest record deal in history. Months after his discovery, he took the stage at Woodstock.
Jerry Garcia
The Grateful Dead founder and lead guitarist is exactly what anyone thinks of when they think of hippie culture. Garcia stole his mom's car, was kicked out of the army, and spent the rest of his life dedicated to music that would shape an entire generation. Garcia's music was known for embodying the jam aesthetic, something that hadn't been done to the Dead's extent before.