Les was also a massive pioneer in recording technology and (of course) guitars. He played every Monday night at Iridium in NYC for nearly 15 years until he passed away in 2009 at 94. A friend of mine and I kept talking about going to see him, but we never found time to do it. Although I know jazz going way back, I was too young (and clueless I guess) to have known Les's playing or really anything about him -- I just thought it would be cool to see the guy who invented the Les Paul guitar. So that's why we never made time to go. If I knew what a great player he was, and what a character he was in the Iridium gigs, I would have literally been there every week.
I only learned about Les from an older bass player that my son plays in a group with. He is very, very good friends with Les' lifelong luthier (the guy who helped do all the innovation in guitars -- though Les would also gouge out wood and do mods himself also). He knew Les also. Through the bass player, I learned what a monster player Les was, and also what a character he was. He has a million Les stories. Not only was Les great, he had a "who's who" of guitar greats that would stop by all the time on Monday nights and sit in on those gigs to pay homage to Les. Fortunately, there's a ton of YouTube videos capturing it.
Here's one with Billy Gibbons (ZZ Top). Les is just a total smart ass, but in a way that just works and is endearing. It's often really hard to tell if he's serious or he's yanking the guest's chain as part of his shtick. For example, when Billy first joins Les on the stage, Les asks "Now, do you play guitar?". Billy could not have been more of a gentleman throughout the whole thing.
This one with Brian May is pretty interesting. It starts with Brian and Les doing a blues tune that sounds great. Brian doesn't really want to call the second tune, but Les urges him on. Then Brian, I guess wanting to suggest a true jazz tune more down Les's alley, suggests "C Jam Blues". Brian want Les to start the tune, but Les says "I don't know how it goes" (that is definitely Les yanking Brian's chain). Then after Brian plays the first few bars, Les asks "what key are you in?" (the answer is C of course, C Jam Blues). Brian struggles on the jazz tune a bit. Afterwards, Les says something like "that's alright Brian, you can't hit it out of the part every time".
Steve Miler brings a Fender strat to play with Les -- lot's of banter of course. Steve sounds great of the first tune. He was smart enough to just sing for the jazz tune (Nature Boy) given Brian May's experience.