Best example for this EXACTLY how you describe it, is James Kottak with his group KOTTAK - played a tour with Blowsight here and barely 30 (!) people showed up! Everybody got the chance to meet James (and Athena back then...) and the band, have a beer or whatever and talk how long people want.
Half a year later and I am supposed to meet James at a SCORPIONS Arena show and there's big backstage hectic and security people around and so on....

Another would be SAMANTHA 7 ( CC DeVille's old band ) featuring Francis Ruiz who is now drumming for Kottak and Ty Longley (Rest in Peace)
who were opening for Great White club shows here in 2003 (?)

And I saw John Waite feat. Kyle Cook (Matchbox Twenty) play infront of maybe 70 people in 2011 a couple of weeks after the later played in Australia for I don't know how many tens of thousands of people...(Andrew would knew this..)

Or Marco Mendoza with his trio Strait Jacket (world class musicians Joey Heredia and Renato Neto) playing some nice blues/jazz inflenced set infront of 40 "pop music students" of which nobody knew who those people were...