Ep 1. Olivia Wilde is Pretty and You're All Disgusting!, with Olivia Wilde

In the season 3 premiere of Billy on the Street, host Billy Eichner goes out into the streets of New York City with guest star Olivia Wilde, best known for her roles in House and Tron: Legacy, amongst others. The episode is titled "Olivia Wilde is Pretty and You're All Disgusting!" which already sets the tone for Eichner's sharp, sarcastic commentary on the streets of NYC.

As always, Eichner remains unafraid to approach strangers and ask them wild and outlandish questions. In this episode, he and Wilde engage in a game called "John Mayer or Pepe Le Pew," where they show strangers a photo of either the musician or Looney Tunes character, and ask them to identify who is on-screen. From there, Eichner and Wilde comment and joke on their responses.

Throughout the episode, other visitors enter into the fold, including the singer-songwriter and Girls star Andrew Rannels, known for his work in musical theater. Together, they play a game in which they ask pedestrians to give their opinions on various celebrities, based solely on the faces of the stars. The game is called "Lena Dunham or Toni Collette" and continues further as they move on from discussing the two of them to including other female stars like Jane Lynch and Sarah Jessica Parker.

But the real highlight of the episode is when Eichner and Wilde approach people with the question “Would You Have Sex With Olivia Wilde?” Eichner usually begins with a ridiculous comment on the physical attractiveness of Wilde like “She's not that pretty, I guess” or “Is her skin too dewy?” before asking people if they would even consider having sex with the star. Some responses are quite interesting and humorous, while some remain mostly uncomfortable as people try to avoid answering.

As always, hilarity ensues as Eichner brings his irreverent sense of humor to the streets. The episode tackles typical celebrity worship head-on and satirizes the whole notion of fandom in the United States. While also providing plenty of laughs and absurd moments, the episode is a scathing commentary on America's obsession with celebrities and the way they are treated in the media.

In this season premiere episode, Eichner and Wilde demonstrate excellent on-screen chemistry as they play off each other's jokes and reactions to the people they meet on the street. Wild is quick-witted and engaging, providing a perfect foil to Eichner's biting humor. As they make their way through the crowded streets, Eichner relentlessly bombards strangers with comedic inquiries, some of which are surprisingly thought-provoking.

Overall, "Olivia Wilde is Pretty and You're All Disgusting!" is a hilarious and well-executed episode that captures the essence of what makes Billy on the Street such a popular and beloved show. Fans of Eichner will enjoy the typically outrageous antics and irreverent humor, while Wilde's undeniable charm adds a new dimension of appeal to the series.