"I have a daughter who doesn't have a mom. I have to paint a picture for Dannielynn of who her mom was," said Dannielynn's dad Larry Birkhead.
Watch the full story on "20/20" TONIGHT at 9 p.m. ET on ABC.
The father and daughter started their road trip in Smith's hometown of Mexia, Texas, which has a population of 7,459.
That's where they met Jo McLemore, Smith's high school best friend, who told Dannielynn she looked just like her momma.
As a teenager in the 80s and 90s, a young Smith -- born Vicki Lynn Hogan -- was determined to make her way out of Mexia.
She found work as a dancer at a Houston strip club where she made a name for herself. In 1991, billionaire investor J. Howard Marshall II came into her club and she would later marry him, despite their 63-year age difference.
Around the same time, she started gaining traction in her modeling career, working with Playboy and Guess. She would eventually move to Hollywood while making a name for herself as Anna Nicole Smith.
Yet Larry Birkhead, who met Smith in the early 2000s while working as a photographer, said he was drawn to her off-camera self.
"You know what her favorite thing was that she used to do? Do you know what a VCR tape is?" he asked his daughter on their road trip.
"Yes," Dannielynn replied.
"She'd go up here to this Blockbuster, and she would rent movies and she would just sit in the bed for the whole weekend and order takeout food. She just loved to stay in and watch scary movies. And then she'd paint," he said.
When the pair stopped in Los Angeles, Larry showed Dannielynn a storage room full of Smith's personal belongings.
"She has a big heart like her mom had, and I think she could appreciate these things," he said.
In Friday's 20/20 special, Birkhead is opening up about the many ups and downs in Smith's life. He said he hasn't held back in how he recounts Smith's life to Dannielynn but said he is conscious in making sure she sees the moments worth celebrating in her life.