His sketches with Elaine May were about thirty years ahead their time and (IIRC I was a kid then and am basing this on memory). They were extremely clever send ups of the same kind of New York neurotics that Seinfeld turned into gold. The sixties really were a golden age for stand up comedy.
They were a big influence on Woody Allen for one thing.
Interesting note on Nichols and May; at one point in their partnership, they were contributors to “Monitor,” the long-running NBC radio program that aired on weekends across the country. Nichols and May provided comedy bits that were sometimes used to fill dead air if there were technical problems with a remote, or a guest didn’t show up.
Nichols and May did most of their Monitor appearances on tape, and it was a long, hard grind to get usable material. Sometimes, they’d spend eight hours in the studio and emerge with nothing that could be put on the air.
Bob and Ray were also on retainer for Monitor. They worked live and could easily fall into one of their classic routines, or ad lib something off the top of their heads. Nichols and May were hilarious in their heyday, but when producers needed something funny to fill some time, they turned to Bob and Ray.