Even though it seems that Donald Trump’s crude remarks about women that was caught in a 2005 recording may have dealt the final blow to his presidential campaign, it’s not the first time the Republican presidential nominee has made sexually explicit comments.

CNN Politics released a list on Saturday of some of Trump’s most inappropriate remarks he made during his many visits to shock jock Sirius XM host Howard Stern’ s program.

During an October 2006 interview, Trump told Stern that his growing daughter Ivanka “looks more voluptuous than ever.”

When Stern asked Trump if Ivanka had breast implants, Trump said, no, “She’s actually always been very voluptuous. She’s tall, she’s almost 6 feet tall and she’s been, she’s an amazing beauty.”

That doesn’t even compare an interview in 2004, when Trump allowed Stern to describe his daughter Ivanka as a “piece of ass.”

“My daughter is beautiful, Ivanka,” Trump said.

“By the way, your daughter,” said Stern.

“She’s beautiful,” replied Trump.

“Can I say this? A piece of ass,” said Stern.

“Yeah,” Trump consented.