Founding King Crimson would’ve been enough to crown Robert Fripp a prog god of the tallest order, but he’s also a contributor and collaborator with the equally esteemed likes of Brian Eno, David Bowie, Peter Gabriel, Daryl Hall, David Sylvian and so many more.

Since 1993, David Singleton has stayed by his side, spearheading their Discipline Global Mobile (DGM) record label, serving as the group’s producer, recording on his own and writing the fiction series “The Vicar Chronicles.”

Together, “That Awful Man and His Manager” pulled up chairs at the intimate City Winery for an almost three-hour conversation with one another and the extremely dedicated crowd, frequently lifting the veil of mystery and perfectionism to reveal a true gentleman, who despite genius status, isn’t afraid to dance around in a tutu as a social media sensation beside his wife and fellow artist on “Toya & Robert’s Sunday Lunch.”

No topic was off limits, but cameras and recording devices were strictly prohibited until the curtain call, which made the generous, humorous and insightful evening all the more exclusive for those who were in the room where it happened.

A few of the many takeaways included Fripp’s extreme focus before a concert that only ever allowed his mother, sister or wife a visit (though cheekily not former drummer Bill Bruford), praise for late multi-instrumentalist Bill Rieflin for bravely battling cancer and a winking realization that singers are always a problem.

He also expressed vehement opposition to several streaming services not properly compensate artists, dubbed American radio “appalling” while praising the university or public stations, explained skipping out on signing autographs in person because of overzealous behavior and no longer conducting interviews due to the repetition of questions.

That didn’t stop fans from inquiring about anything they wanted, ranging from rare factoids on classic recording sessions dating back to 1967, differing techniques between the analogue and digital eras or swapping creative philosophies, such as drawing a parallel to the necessity of food for the body and music for the soul.

The headliner instantly put the most nervous guests at ease and listened intently to a man tearing up over a lifetime of impact, followed by a woman who didn’t play an instrument, but nonetheless shared her uplifting observations from his book, “The Guitar Circle.”

Ladies always got to skip the line and Fripp even apologized at one point for a lack of gender inclusivity in the term “master musician,” which earned a few rounds of debate from an onlooker who apparently opposed the idea before the subject was politely changed avoid it escalating into a scene.

However, everyone could agree on the band’s unmatched abilities during film clips of “21st Century Schizoid Man,” taped in front of 100,000 people at 2019’s Rock In Rio, plus “Fracture” and “Starless,” performed privately in a train station for the forthcoming documentary, “In The Court Of The Crimson King, King Crimson At 50.” 

Singleton suggested there would be more archival releases in the pipeline, but studio material from the final incarnation would be unlikely, further supported as Fripp outlined three reasons any scenario might come to an end, which include a loss, reaching a natural conclusion or successfully completing the task at hand.

In the case of King Crimson, it was absolutely the latter reason, and while it remains to be seen where the next chapter will lead, all of City Winery clearly concurred this mission was accomplished to the most inventive extent possible in the meantime.

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For additional information on Robert Fripp and King Crimson, visit DGMLive.com.

Upcoming concert highlights at City Winery include John Prine Birthday Celebration (Oct. 10); Major. (Oct. 11); Jennifer Hartswick Band (Oct. 12); Meagan McNeal (Oct. 14); Beatles Brunch (Oct. 16); Cocktales (Oct. 16); Hi-Five (Oct. 17); Acoustic Alchemy (Oct. 19); Candiace (Oct. 20); Chrisette Michele (Oct. 23-24); Jackie Evancho Sings Joni Mitchell (Oct. 25); I Am Athlete (Oct. 27); Bob Schneider (Oct. 28); Jon McLaughlin (Oct. 29); Shanice (Oct. 30) and Just Fine: The Ultimate Mary J. Blige Tribute (Oct. 31). For additional details, visit CityWinery.com/Chicago.