"No, no, no, no, no! You are not doing this! You are not 9/11-ing your dick pics!" Oliver said. "... In fact, maybe you should just stop talking altogether and hire a professional communications director to do that for you."
That, of course, didn't go so well, either. On Tuesday night, Weiner's communications director, Barbara Morgan, went on an epic tirade against a former intern who had written an unflattering tell-all about the campaign, calling her a "slutbag."
This all led Oliver to make a point about Weiner's candidacy.
"What is Anthony Weiner going to do? Fire her for inappropriate behavior?" Oliver said.
"He can't do that! And that is why he won't be able to run this city. He has no standing to punish anyone for anything anymore."
Watch the clip below, in which Oliver also goes after the embroiled-in-scandal San Diego Mayor Bob Filner: