The HBO host took aim at Leno’s recent complaint about a perceived lack of “civility” from late-night hosts such as Stephen Colbert, Jimmy Kimmel amid the genre's heavily political climate.
“You know, everything now… everyone has to know your politics,” Leno told the “Today Show” last week. “I tried to use Johnny’s model, and I would get hate mail from both sides equally and thought ‘well that’s fabulous, that’s exactly what I want’.”
“But when people see you as one-sided, it makes it tough. And, you know, I did it when Clinton was horny and Bush was dumb, and it was just a little easier."
He added: “Now it’s all very serious, I’d just like to see a bit of civility come back to it."
Oliver didn’t seem to appreciate the critique coming from Leno and took a shot at the former “Tonight Show” host during a segment about public shaming.
The 41-year-old comedian said he believes some good can come of public shaming, before admitting he himself has gone too far — including a Monica Lewinsky joke he was part of during a 2008 episode of “The Daily Show.”
Oliver admitted the bit was “gross,” before mentioning other comedians have since apologized for how they treated Lewinsky at the time.
He then turned his attention to Leno, who has not apologized for jokes he made about Lewinsky during her scandal.
"Many comedians have since expressed regret about things they have said about her, although one who hasn’t – and was among the most relentless – was Jay Leno,” he said.
Oliver then showed a montage of old jokes Leno made about Lewinsky, including one about DNA samples and another about the former White House intern having “sticky” clothing.
“Those jokes have not dated well in any sense of the word. And they are pretty rough, especially coming from a guy who just this week complained about late night TV saying that he would like to see ‘a bit of civility come back’,” the “Last Week Tonight” host said.
“You know, like that time he did a bit with a fake book about Lewinsky titled 'The S--t in the Hat.' And if that’s what he means by civility, may I offer my new book: 'Oh, the Places You Can Go F--- Yourself, Jay Leno!’”
Oliver’s comments came after Leno wasn’t the only person to bemoan the current state of late-night TV, with President Trump adding his own criticisms.
Trump fired off the latest salvo in his long-running late-night war last Thursday morning, attacking ‘the three very and untalented’ late-night hosts.
It is assumed the president was referring to Jimmy Kimmel and Stephen Colbert, who both mocked him on their shows Wednesday night, and Jimmy Fallon.
One day earlier, the president slammed the “very boring” shows by picking up on comments made by former “Tonight Show” host Jay Leno, who bemoaned how political the genre has become.
“The one-sided hatred on these shows is incredible and for me, unwatchable. But remember, WE are number one - President!” Trump tweeted.