Dr. Wolfe is the rogue periodontist who owns a dental and orthodontic clinic called "Painless Dentistry".
He is known for being able to tell when people are lying, and will vehemently call them out on it. He informs Marge that Lisa needs braces, at exactly the same time that Mr. Burns revokes Homer's dental plan. Unable to pay for good braces, Dr. Wolfe gives Lisa a set that "predate stainless steel". However, Wolfe is notably horrified as soon as the procedure was completed at what he gave Lisa, remaining speechless when Lisa demands for the mirror twice, handing it to her after she demands the mirror the second time around, and backs away in fear as Lisa starts laughing maniacally in a brief loss of her sanity and smashes the mirror to pieces when she sees the new braces. In the end, Homer gets the dental plan.
Dr. Wolfe is last seen laughing about leaving the gas on, and the rest of the family (along with Dr. Wolfe) collapse as a result of inhaling too much. While he has not been seen since, Marge later discovered that he was not actually a qualified orthodontist, but a rogue periodontist, requiring Lisa to get braces again.
Behind the Laughter
Anthony Perkins had agreed to voice Dr. Wolfe, but unfortunately fell ill and could not record the part. Clint Eastwood and Anthony Hopkins had also been asked to provide a voice, but both declined. Dr. Wolfe's reaction to the aftermath of the procedure, as well as the scene itself, spoofed the aftermath of Jack Napier's botched reconstructive surgery in the 1989 Batman movie.