This latest Trump misstep to emerge -- a 2005 video released by The Washington Post on Friday -- is perhaps the most shocking to date, and doubtless the most vulgar.
The revelations threw his campaign, and the Republican Party as a whole, into disarray just one month before Election Day on November 8, and on the eve of his second presidential debate with Democratic nominee Hillary Clinton.
Trump backs off praise of Russia's Putin after debate
With mounting calls inside his own party for him to step aside, Trump made a video apology -- the first of his campaign. But it was ambiguous. "I've never said I'm a perfect person, nor pretended to be someone that I'm not," he said, his brow furrowed.
Then he added: "I've said and done things I regret, and the words released today on this more-than-a-decade-old video are one of them."
This comment came as part of a yearslong series of crude conversations about women that Trump had with radio host Howard Stern, who has a longtime reputation as a provocateur. CNN's KFile investigative unit released the newly uncovered audio Saturday.
Trump can be heard discussing his daughter Ivanka's physique, having sex with women on their menstrual cycles, threesomes, and leaving a relationship after women turn 35.
"She's actually always been very voluptuous," Trump says in an October 2006 interview about his daughter when asked by Stern if she had gotten breast implants. "She's tall, she's almost six feet (1.8 meters) tall and she's been, she's an amazing beauty."
In the Stern interviews, Trump frequently discusses details of his sex life.
In a 2006 interview, Trump -- then 60 years old -- says he would have no problem having sex with 24-year-olds.
In an April 2005 episode, Trump suggested he may have had sex with Miss Universe or Miss USA contestants. Trump has been an owner of both pageants.
Asked if he would accept a contestant's request to have sex with him, Trump responds: "I don't want to hurt their feelings."
"Well, what you could also say is that, as the owner of the pageant, it's your obligation to do that," Trump says, adding that he's gotten away with going backstage when the contestants were naked.
Trump made those derogatory comments about his former Republican primary opponent Carly Fiorina.
When a moderator probed Trump about the comments during a televised primary debate, Fiorina quipped: "I think women all over the country heard very clearly what Trump said."
The bombastic Republican described Fox News journalist Megan Kelly with those words after she moderated a Republican primary debate last August.
He later tweeted that he was referencing Kelly's nose.
Trump made these recent comments after the Clinton campaign brought Venezuelan-born Alicia Machado, a former Miss Universe, into the spotlight to highlight derogatory remarks Trump made toward her.
Trump apologises for his crude remarks in 2005 video
Machado said the billionaire bullied her mercilessly after she won her crown, calling her "Miss Piggy" after she gained weight.
In an effort to woo the female electorate, Trump threatened to drag ex-president Bill Clinton's sex scandals into the White House campaign, hoping that talking about the sexual exploits that stained the career of Hillary's husband Bill would turn female voters away from her.
In 2006, Trump hurled those insults at actress Rosie O'Donnell, who has been the real estate magnate's arch-nemesis for at least a decade.
Trump mocked The Huffington Post's co-founder Arianna Huffington in 2012, after her ex-husband announced he was gay following the couple's divorce.
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