Rosie O’Donnell Fires Back At Donald Trump, Delivers The Best Insult Of 2016

Rosie O’Donnell and Donald Trump have a long history of hating each other. The public had pretty much forgotten about Trump’s rude comments about O’Donnell’s weight and appearance until they resurfaced during Monday night’s presidential debate.

Hillary Clinton broached the topic during the debate by bringing up Trump’s history of saying disparaging things about women. “This is a man who has called women pigs, slobs, and dogs,” Clinton said during the debate, “and someone who has said that pregnancy is an inconvenience to employers.”

Although Trump did call O’Donnell a pig in the past, Clinton didn’t specifically mention the comedy actress by name. Instead, the Democratic candidate opted to bring up Alicia Machado, a beauty contestant that Trump once called “Miss Piggy” after the participant put on weight and “Miss Housekeeping” due to her Hispanic heritage.

Donald Trump trying to defend his comments about women at Monday's presidential debate. [AP Photo/David Goldman]

O’Donnell appears to be an easy topic to for Clinton to bring up given the public nature of Trump’s feud with the former TV show host, but Clinton played her cards conservatively. Instead of stating the obvious, Clinton let Trump do the work for her. In Trump’s rebuttal to Clinton’s assault, the Republican candidate did more harm than good to his own image.

Trump responded, “Hillary is hitting me with tremendous commercials. Some of it I said in entertainment, some of it said to somebody who has been very vicious to me, Rosie O’Donnell. I said very tough things to her and I think everybody would agree she deserves it and nobody feels sorry for her.”

The feud between O’Donnell and Trump reached a fever pitch in 2007 when Trump appeared on Larry King Live to discuss his latest book at the time, “Think Big and Kick Ass In Business and In Life.” According to CNN, Trump accused O’Donnell of eating “like a pig” at the real estate mogul’s 1993 wedding to Marla Maples and insulted the comedian’s intelligence.

Rosie O'Donnell Donald Trump

During the interview with Larry King, the host read an excerpt from O’Donnell’s own book detailing her dislike for Trump. King quoted the book saying, “I kept Trump products in my office because they reminded me that my attacker was not a human being, but a wind up toy with Tourette Syndrome — a man who had allows himself to get pulled so deeply into capitalism that he turned his entire being into a product with a price tag on it. He was gift-wrapped and stuffed with Styrofoam.”

Trump responded in the 2007 interview, “Do you think she wrote that? I have a feeling she didn’t write that. I don’t think she writes that well. Her book is not doing very well, by the way.”

Although Trump reintroduced O’Donnell to the general public, the former The View star wasn’t going to go down without a fight. During the debate, O’Donnell immediately took to Twitter to proclaim that “HE WILL NEVER BE PRESIDENT” in reference to Trump.

O’Donnell then shared an old clip of The View where she explained her initial problem with Trump and the Miss USA pageant. That’s when she released the best Trump insult of the presidential debate by saying, “— the 5 mins orange anus can’t seem to get over — tell the truth – shame the donald #I’mWitherHer”

Rosie wasn’t alone in her indignation. A number of celebrities, including A League of Her Own co-star Madonna, defended Rosie as well as Lena Dunham, Seth MacFarlane, and Leslie Jones who also rallied behind Rosie. O’Donnell’s call to “shame the Donald” worked better than she could have expected and rekindled the public’s awareness of Trump’s misogynist remarks about women.

Trump got away with mentioning O’Donnell during the Republican primary debates, but in a one-on-one setting against Hillary Clinton, the topic didn’t suit him well. He has a history of bashing O’Donnell, both in interviews and on the debate stage, and it comes off as unpresidential and unappealing for the Republican candidate.

[Featured Image by Charles Sykes/Invision/AP Images]