Friday, Donald Trump’s crude and repulsive statements about women from 2005 may have dealt a death blow to his campaign for president, but the former reality TV star has engaged in sexually explicit banter publicly on a number of occasions in the past.

On Saturday, CNN Politics published a rundown of some of Trump’s most uncomfortable, inappropriate and lewd remarks to shock jock Sirius XM host Howard Stern.

In October 2006, Trump told Stern that his developing daughter Ivanka “looks more voluptuous than ever.”

Stern asked if Ivanka had received breast implants, to which 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.”

Listen to audio of the clip, embedded below:

In September of 2004, Trump was even cruder in his remarks about Ivanka when Stern asked if Trump was comfortable with Stern calling his daughter 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 assented.