Season 5
10 episodes · first aired 2016-11-15
| Still | # | Title | Overview | Air date | Rating |
|---|---|---|---|---|---|
 | 01 | Immigrant or Real American? with Jon Hamm 2016-11-15 | 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. | 2016-11-15 | 8.0 |
 | 02 | Death Rogen with Special Guest Seth Rogen! 2016-11-22 | 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?" | 2016-11-22 | 6.0 |
 | 03 | Lupita Nyong'o: Bring the Pain 2016-11-29 | 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! | 2016-11-29 | 7.0 |
 | 04 | Miracle on 34th Streep with Andy Samberg! 2016-12-06 | 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?". | 2016-12-06 | 7.0 |
 | 05 | Aziz on the Street! 2016-12-13 | 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!" | 2016-12-13 | 0.0 |
 | 06 | Billy's Holiday Wonderland with Jacob Tremblay! 2016-12-20 | 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." | 2016-12-20 | 0.0 |
 | 07 | Do Gay People Care About John Oliver? with John Oliver! 2017-01-03 | John Oliver joins Billy out on his street ventures. Billy asks gay people what they think about the famed English comic and host. | 2017-01-03 | 0.0 |
 | 08 | Curbside Conga Line with James Corden 2017-01-10 | 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." | 2017-01-10 | 7.0 |
 | 09 | Super Sloppy Semi-Automatic Double Dare! with Keegan-Michael Key 2017-01-17 | 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." | 2017-01-17 | 0.0 |
 | 10 | The NY Bubble with Stephen Colbert! 2017-01-24 | 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. | 2017-01-24 | 0.0 |
Ratings shown are community scores. Once OMDB is wired, these become per-episode IMDB values.