Season 5

2016-11-15 · 22m

Billy and Jon Hamm take to the streets to find out if anyone will have a threesome with them! Later, Billy plays "Immigrant or Real American?" with Kevin the bisexual office manager.

2016-11-22 · 22m

Billy hits the streets with Seth Rogen for a new segment called "Death Rogen". Later, just in time for Thanksgiving, Billy and Sarah play "What Does Michelle Rodriguez Bring to the Table?"

2016-11-29 · 22m

Billy is joined by Oscar winner Lupita Nyong'o for the brand new game, "Gay or Old?" Later, everyone's favorite contestant, Elena, is back with a very patriotic Lightning Round!

2016-12-06 · 22m

Billy and Andy Samberg play the new game "Was at My Wedding or Possibly Killed Tupac?"; Billy and Andy introduce New Yorkers to some new superheroes; Kevin the busboy joins Billy to play "Fox News Anchor or Pilgrim?".

2016-12-13 · 22m

Billy is joined by Aziz Ansari to play the brand new game "Is This a Kanye West Quote or Not?". Later, Rachel Dratch is back for an exhilarating obstacle course, "Escape Margot Robbie's Moment!"

2016-12-20 · 22m

Billy is joined for the first time by a child actor, the star of "Room," Jacob Tremblay. Together, Jacob and Billy take to the street for a brand new "Lightning Round."

2017-01-03 · 22m

John Oliver joins Billy out on his street ventures. Billy asks gay people what they think about the famed English comic and host.

2017-01-10 · 22m

Talk-show host James Corden helps Billy appeal to the masses; Billy and actor Robin Lord Taylor ("Gotham") play an obstacle course called "Can You Separate the Art from the Artist?"; other games include "For a Dollar."

2017-01-17 · 22m

Billy is joined by Keegan-Michael Key for the game "Name 10 Gay People"; aspiring actor Cameron plays "Walking Dead or Talking Dead?"; Key competes in a new obstacle course; other games include "For A Dollar" and "Give It Up For Kate Hudson."

2017-01-24 · 22m

Billy welcomes Stephen Colbert to play "La La Land or Nicki Minaj", and Stephen heads out onto the streets to ask how New Yorkers feel about Donald Trump. Plus, Elena returns to answer Twitter questions.