5 of the best 'Ashlee Simpson Show' moments, from Ryan Cabrera kisses to that notorious 'SNL' appearance

Raechal Shewfelt
Editor, Yahoo Entertainment
Ashlee Simpson-Ross in 2018. (Photo: Tiffany Rose/Getty Images for Ciroc)

Ashlee Simpson will soon be back on the air.

E! has announced plans for an upcoming docuseries featuring Simpson (who now goes by Simpson-Ross) and husband, Evan Ross, as stars of and co-executive producers, following their lives as new parents and music artists creating an album of duets.

The series marks her grand return to reality TV, since the binge-worthy Ashlee Simpson Show on MTV ended in 2005. Over 18 episodes, viewers followed the “Pieces of Me” singer as she romanced fellow singer Ryan Cabrera, struggled with figuring out who she was as an artist and a person (definitely not one of those other blonde singers, OK?!), and did all the goofy things that a 19-year-old does, all for our viewing pleasure.

Here are some of the most memorable moments from that fantastic piece of pop culture history.

1. Ashlee’s first kiss with Ryan Cabrera.

Credit:  Ashlee Simpson Show

The audience caught the exact moment when Simpson first kissed Cabrera, because it happened as she co-starred alongside him in his video for his hit 2004 song “On the Way Down.” As Simpson explained in one of the side interviews she did throughout the show, Cabrera had become her “best friend” after living with the Simpsons for more than a year. He asked her to play his girlfriend and, during one of the takes, Simpson just couldn’t stop herself from throwing him up against a wall and kissing him. “He was in so much shock,” she said with a laugh. And then they fell in love. Aww.

2. She goes to the dark side.

Credit:  Ashlee Simpson Show

In one episode, Simpson makes a statement by switching up her hair. “I decided to dye my hair because I just needed to do something new, and I kind of, like, wanted to do something spontaneous and shock everybody,” she said. “I didn’t do it to separate myself from my sister, but it’s a lot of fun, because she’s got this platinum blonde hair and I’ve got this really dark hair.”

Simpson’s yearning to step out of her famous sister’s shadow was also documented on the show, especially when she wrote the song, “Shadow,” about this very subject.

3. She disses Hilary Duff.

Jessica wasn’t the only pop star Ashlee didn’t want to be compared to as an artist. She also name-dropped Lizzie McGuire star Hilary Duff on more than one occasion.

Credit:  Ashlee Simpson Show

4. The Saturday Night Live debacle plays out.

When Simpson was infamously caught lip-synching on Saturday Night Live in 2004, fans of her show saw the doctor’s visits that led up to it. She’d struggled with acid reflux and damage to her vocal cords right before the all-important gig. Viewers also saw the cringeworthy aftermath — the paparazzi tailing her and the awkward interview moments — years before Twitter was around to make the backlash even worse.

5. Jessica gets a bug in her hair.

The day that Ashlee and Jessica worked together to film a commercial for Pizza Hut, Jessica had a bit of a chicken or fish moment, when a bug landed in her tresses. The Newlyweds star managed to steal the spotlight away from her little sister on Ashlee’s own show.

Credit:  Ashlee Simpson Show

With Jessica busy dominating the fashion world, it looks like this time, Ashlee will have TV all to herself. But maybe she can get still get big sis to do a cameo for the first episode.

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