Reggie's right in observing that personal charisma/persona is the key, along with song selection.

In my own long-ago experience, I did much better in San Francisco (my summertime base of operations), where I more-or-less fit the tourists' expectations of seeing jen-you-wine hippies. This was 1971/72, when the "real" hippies had all fled the city; as a johnny-come-lately longhair from Back East, I served to fill the bill. I never fared quite as well during the cooler half of those years in New Orleans -- nor did any of the other solo performers I knew -- where folks were more predisposed to seek out and enjoy musical *groups.* There were trad-jazz combos out on the street, who matched those expectations almost exactly, but jug bands and bluegrass groups did well too.

As far as song selection is concerned, you need to have a varied repertoire at your fingertips, including some contemporary stuff. That may not be true in all cases, especially if you play an "exotic" instrument associateed with a particular tradition, e.g., bagppipes, mountain dulcimer (or hammered for that matter), even banjo. But if you're doing plain vanilla guitar-and-vocals, you'd better have a full set of tricks up your sleeve.

If you can catch the eye and engage the attention of *anyone* and induce them to stop and listen, it will often have a "snowball effect." That is, other passersby who notice any kind of byplay, flirtation, whatever, may be intrigued enough to hang around to see what happens next. If you can ad-lib between numbers to heighten interest, so much the better. Better yet, if you can perform a song during which you can lift an eyebrow or mime a doubletake at a particular line of the lyric, go for it!

My brother just put me hip to a website with lyrics and tablature for many tunes in which he and I share an interest. He has much more experience as a professional musician than I do -- 12 or 15 years as a drummer with nary a day job -- but is only recently born again as a guitar player. I get a kick out of seeing his enthusiasm at learning a new instrument. Anyway, here's the link:

www.rukind.com

This is where he learned his first fingerpicking piece, the Beatles' "Blackbird." He reports that the site provides plenty of "classic-rock" era favoritres, including lots of Beatles, even more Bob Dylan, some Stones, etc., plus "everything ever recorded by anyone ever associated with the Grateful Dead." (Those in the know may have already recognized "Are You Kind" as a G.D. reference.) For those of you not interested in the Dead, I should point out that some of the members had extensive previous experience in folk music and bluegrass, and the "rukind" database includes plenty of traditional folk, blues, jug band, bluegrass, country, rockabilly, etc. There's probably a good deal of overlap with the DT here at Mudcat, but DT doesn't provide tablature (??) -- at least not for very many tunes.

The songs available there would not include any very-recent stuff (some of which you should have ready to perform), but does include a good selection of material familiar to us "baby-boomers," still a very large demographic category with disposable income. Well, disposable change, anyway.