I don't think this pick needs too much explanation. There are three people in this singer-songwriter category I considered equally worthy of the #1 pick, but in my opinion Bob Dylan is the greatest recorded singer-songwriter who ever lived. He's had a massive career spanning nearly FIFTY years, with multiple creative peaks. His songwriting is innovative and brilliant, full of hazy, surreal imagery, personal confessional lyrics, funky and innovative rhyme scheming, and influence drawn from all walks of music.

He was always one step ahead of the curve. He rose to prominence as a leading light of the folk movement, but he saw where the future was headed and moved to electric at a time when it was wildly unpopular for him to do so. He introduced some of the leading acts of the 1960s to the drugs that fueled their creative expansion of consciousness. His live performances in his younger days were among the most electric and exciting around (think the "Royal Albert Hall" performance of 1966, which I can't find on youtube but really wish I could).

His influence was felt by numerous acts of his day and beyond, some of the greatest musicians of all time, and it's a shame I can't name them. His collaborative efforts with certain groups have been among the best work of their careers. Other artists' covers of his songs have become among the most notable of their work, which speaks worlds to his abilities as a songwriter.

He had three distinct creative peaks-- a sick run in the 1960s (highlighted IMO by Blonde on Blonde and Highway 61 Revisited, both of which belong on short lists of the greatest rock records of all time) a resurgence in the mid-70s with the weary-hearted breakup album Blood on the Tracks, and then again as an old man looking back on life at the turn of the century with Time out of Mind and Love and Theft. Even when he had some strange missteps (Saved lol), he was always thinking forward, always trying to push the envelope as to what popular music could be.

Simply put, there's not a doubt in my mind that Bob Dylan is the finest songwriter who ever lived, and he was the one guy I wanted to build my studio around more than any other. The man is nearly 70 and still putting out music and touring. I can only think of one other individual who's maintained remotely that sort of popularity through the last fifty years, and I'd be shocked if he didn't go in the next two or three picks.

In fact, the only disappointing thing about him is the lack of material he has on youtube. Here's one more for the road.

Short answer: Bob Dylan is the GOAT. I got him at #3. I got the steal of the draft.