Season 5
10 episodes · Nov 15, 2016
Season Videos
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S5E1Immigrant or Real American? with Jon Hamm
Nov 15, 201622mBilly 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.
S5E2Death Rogen with Special Guest Seth Rogen!
Nov 22, 201622mBilly 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?"
S5E3Lupita Nyong'o: Bring the Pain
Nov 29, 201622mBilly 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!
S5E4Miracle on 34th Streep with Andy Samberg!
Dec 6, 201622mBilly 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?".
S5E5Aziz on the Street!
Dec 13, 201622mBilly 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!"
S5E6Billy's Holiday Wonderland with Jacob Tremblay!
Dec 20, 201622mBilly 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."
S5E7Do Gay People Care About John Oliver? with John Oliver!
Jan 3, 201722mJohn Oliver joins Billy out on his street ventures. Billy asks gay people what they think about the famed English comic and host.
S5E8Curbside Conga Line with James Corden
Jan 10, 201722mTalk-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."
S5E9Super Sloppy Semi-Automatic Double Dare! with Keegan-Michael Key
Jan 17, 201722mBilly 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."
S5E10The NY Bubble with Stephen Colbert!
Jan 24, 201722mBilly 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.