Was there ever a moment when Stern was regular radio?
When a guest of staff person was swearing so much, that he himself cut to a commercial?
Not that I can recall. But one of the closest was when he had on Jackie Stallone and her ex-husband called in
No,because they would just run little bits of silence or build delay into the show very quickly if that happened. There were some times Howard had guests in the studio where he dumped out of entire sentences repeatedly. But never enough to run through the entire delay. The delay is really long.
Kinison was notorious for just dropping 'fuck' and 'cock' and 'pussy' over and over without even realizing it because he was often shitfaced beyond belief. And that was in the late 80s when the delay was well under one minute. By the early 90s the tape delay was pretty long. You'd call into the show and they'd be minutes ahead of you.
They played an old tape of a mafia rat being interviewed recently on MTT I think. The callers kept breaking his balls saying that they'd kill him. "I'd fucking bash your head in with a tire iron". "Talk shit over the radio fucking tough guy". Not even close to hitting the end of the delay.
Even on Sirius the delay is insane. A good five minutes even. On O&A, Opie said he finished the show, got his jacket on, talked to management, left the Sirius building, walked to his apartment, got into his room, turned on his radio, and heard himself saying on the radio "we'll see you tomorrow". That's how long the delay is. He had time to walk to his apartment before the show ended over the air.