Making people break in his pipes? Unlikely. They would have done so willingly, with pay. Time honored tradition in London and Paris a century or longer ago.
I agree, though, that the conversation might be difficult.
They would have been paid and agreed to do it, but he still would have viewed it as making them do so, and taken some level of amusement from it.
Mark Twain is a strange case. He was born in Missouri not long after the Missouri compromise, but before the Kansas-Nebraska Act could totally take its course. He got stuck in the Confederate military and abandoned his post, heading North.
He was disgusted by wealth, and yet he reveled in it. He accidentally invented stand-up comedy by doing after-dinner chats to groups of extremely wealthy men. As much as he denigrated them, whenever he had money he tried to invest it and would go bust. The only notable exception is when he invented the door to door book selling campaign for Ulysses Grant's memoir, but even then he was doing so to try to help Grant provide for his family since he was dying of cancer. Even in his sweetest moments, he always tasted the bitters first and foremost.
He took big swings at wealthy men in his writing, but his best friend was Henry "Hellhound" Rogers, formerly of Standard Oil (Rockefeller)fame. He also looked down on anyone who was willing to be walked on. It put him in a strange and cynical position, one which encourages comedy, but it does not encourage much belief in humanity. He was brilliant, but cynical. If one were to believe in reincarnation, one might think that he and Flannery O'Connor were the same person.
I don't believe he was a terrible person. But to the point by
@crashthegrey if you're not cynical, you would not enjoy conversing with him. But at the same rate, if you're a fan of gallows humor, he'd be a hoot without doubt. Still, he'd do all the talking.
P.S. My answer to the topic question... if it has to be a pipe smoker, I'd smoke a pipe with Andrew Jackson. If I could say any smoker in general, Bruce Lee.