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- Bill Hader plays "Make That Noise" and "Streaming or Screaming". A man plays Amateur Speed Sketching and must draw Angelina Jolie. Actress Amy Sedaris tackles the Shondaland obstacle course. (en)
- Games include: "Humpy Dumpy or Mary J Blige", "For A Dollar," "Quizzed in the Face", "Olivia Wilde is very pretty and you're all disgusting," "You can't do that on television, Adele Edition," "Lighting Round," "Twitter Questions"
Special guest: Olivia Wilde (en)
- Games include: "Lana del race for a cure", "For a Dollar", "Is this or Isn’t this adorable", "She talented or she seems nice" and "Missed Moments"
Special guest: Nick Offerman (en)
- Games include: "Quizzed in the Face", "Did you hear Madonna Died?" and "Amateur Speed Sketching" (en)
- Games include: "Steve Harvey or Harvey Milk", "For A Dollar", "Screaming Tweets", "Cash Cow", "Quizzed in the Face", "Tyler Perry or Art" and "HBO Girls or Berenstain Bears"
Special guest: Lena Dunham (en)
- Andy Samberg plays "Was At My Wedding or Possibly Killed Tupac", then helps Billy rally for blockbuster franchises around lesser known characters with special appearances by Jon Hamm and Lupita Nyong'o. Also: "Fox News Anchor or Pilgrim", and Billy has New Yorkers pretend to have an animated squirrel on their shoulders. (en)
- Games include: "Black Eyes Peas or Black guy who peed", "Angry Turds" and "Dead or Boring"
Special guest: Rashida Jones (en)
- After a very specific guessing game called "Hummus or Nipples?", Julianne Moore uses her acting skills to get tourist tips around Times Square. Other games include "Quizzed in the Face" with Elena and the Gospel Choir Lightning Round. (en)
- Other segments: "Nicole Kidman Rally" and "Moments Never Seen"
Special guest: Kristen Johnston (en)
- After feeling the pressure to list the names of Latino performers in one minute, Tina Fey widens her network by finding new pals around New York. Also: "Bob Dylan or a**l sex" and "The Lightning Round". (en)
- Sarah Jessica Parker gives out shoes with Billy in a special game of "For a Dollar" before guessing between reindeer names and sex apps. Other games include "Kevin Hart or Gabby Giffords" and "Hansel or Gretel", and Billy talks to New Yorkers about the new movie, The Chipmunks RoadChip. (en)
- Games include: "Would Drew Barrymore like that?", "Scream for an American Girl Doll" and "Quizzed in the Face"
Special guest: Will Ferrell (en)
- Actress Anna Kendrick guesses Katy Perry's cat's interests, then helps Billy in his search for love by swiping right or left on real-life people. Also "Quizzed in the Face" with Elena and "Adam Sandler Movie or Gay Bar". (en)
- Under pressure, Keegan-Michael Key attempts to name ten famous gay people. Later, he is subjected to an obstacle course where he must find weapons in "Super Sloppy Semi-Automatic Double Dare". Also: "Give It Up for Kate Hudson" and "The Walking Dead or The Talking Dead?". (en)
- Games include: "Train song or Mommy blog", "Chris Brown or Serial Killer", "Quizzed in the Face" and "Amateur Speed Sketching" (en)
- Jon Hamm and Billy look for sexually adventurous people in a game called "Would You Have a Threesome with Me and Jon Hamm?". Billy asks an office manager to play "Immigrant or Real American?". Tina Fey plays "Man or Woman?". Also: Quizzed in the Face Express and The Lightning Round. (en)
- John Oliver hits the street with Billy to find out if gay people care about him in "Do Gay People Care About John Oliver?", then plays a different version of whack-a-mole called "Whack-a-Joel". Elena joins Billy to talk to pedestrians about the new Star Wars film, Rogue One. Also, Billy asks New Yorkers to pay tribute to the TV series "Bones" in "A Farewell to Bones". (en)
- Games include: "Who Dat?", "Quizzed in the Face", "For A Dollar", "Pink, Meryl Streep, or Who Cares?", "The Price feels so Right" and "This or Talk to Mario Lopez"
Special guest: P!nk (en)
- Billy helps young actor Jacob Tremblay flaunt his fame on the street. Debra Messing returns for a special Christmas edition of "It's Debra Messing, You Gays!". A tourist from Utah plays "Match the Publicist to the Client". Billy visits unique holiday displays in "Billy's Holiday Window Wonderland". (en)
- Games include: "Julia Roberts-Themed Obstacle Course", "Would you Masturbate To Them?" and "Weekend at Bernies or Django Unchained"
Special guest: Rachel Dratch (en)
- Games include: "Would this disappoint Bill Cosby", "For A Dollar", "Quizzed in the Face", "Where does this Stephen King novel take place", "Would You Have Sex with Paul Rudd" and "Clueless or Childless"
Special guest: Paul Rudd and Amy Poehler (en)
- Games include: Premiere of "Quizzed in the Face", "Get In the Snuggie" with Rachel Dratch and "Amateur Speed Sketching"
Special guest: Rachel Dratch (en)
- Stephen Colbert plays a game of "La La Land or Nicki Minaj", and then joins Billy to ask New Yorkers for their messages to President Trump and about living in the New York Bubble. Elena joins Billy to answer fans' Twitter questions. Also: "Melissa McCarthy or My Niece at Chuck-E-Cheese?". (en)
- Games include: "She Clucks or She Sucks", "For A Dollar", "Would Lena Dunham F*** that Cartoon Character", "Quizzed in the Face", "The Vaginal Four", "Lighting Round" and "Twitter Questions"
Special guest: Seth Meyers (en)
- Games include: "Quizzed in the Face", "For A Dollar", "It Gets Better or Better Off Ted", "Billy's Fashion Review" and "Its Spock! Do You Care?"
Special guest: Zachary Quinto and Julie Klausner (en)
- Games include: "Pretty or Liar", "Media Mogul or Rabbi" and "Quizzed in the Face"
Special guest: Nas and Ashley Benson (en)
- Games include: "Quizzed in the Face" with a special guest, and "Children's TV Show from the 80's or a Musician?"
Special guest: Joan Rivers (en)
- Rachel Dratch goes through a rigorous Scientology-inspired obstacle course. Will Ferrell and Billy try to find people well-versed in holiday movies in the Lightning Round. Other games include "Gay, Part-Black or Cokehead" and "Who Discovered this Person: Judd Apatow or P. Diddy?". (en)
- Games include: "Queen Latifiah or Brave Person", "For a Dollar", "Thanks for Sharing Adam Levine", "Billy rants about Ratatouille", "Does Shakira know what that is" and "Meryl-Go-Round"
Special guest: Patton Oswalt (en)
- Games include: "For A Dollar", "Sho Nuff or no he Didn't" and "Where in the world is John Mayer's Penis" (en)
- While discussing his films, Jason Sudeikis ruffles Billy's feathers and plays a game of "Is Beyonce Scared Of That?". Billy and Jason then rally a group of bros. Also: "Quizzed in the Face" and the Lightning Round. (en)
- Games include: "Quizzed in the Face", "Where in the World is Rihanna's Rihgina", and "New Year's Eve or Deformed"
Special guest: Andy Cohen (en)
- Games include: "Quizzed in the Face", "Rapper or Nic Cage Character?" and "British Person or Scientologist?"
Special guest: Mark Hoppus (en)
- Games include: "BuzzFeed List or Schindler's List", "For A Dollar", "Quizzed in the Face", "Passion Of The Christ Lightnig Round", "Mo'lympics" and "Twitter Questions"
Special guest: Joel McHale (en)
- Games include: "Their Bodies, Themselves" and "Tyler Perry Movie Quote or Applebees"
Special guest: Maya Rudolph and Rashida Jones (en)
- Games include: "Quizzed in the Face", "For A Dollar" and "Missing Testicle or Extraterrestrial?" (en)
- Games include: "For A Dollar", "Racist or Vegetarian", "Quizzed in the Face", "How I Met Your Mother Lighting Round", "How I Met Your Mother Car Thrashing" and "Twitter Questions"
Special guest: Neil Patrick Harris and Lindsay Lohan (en)
- Games include: "Quizzed in the Face" with a secret twist, Premiere of "Cash Face" and Billy releases his inspired James Blunt inspired single "You Look Really Good For You" (en)
- Games include: "Chipmunk or Huxtable", "For A Dollar", "Quizzed in the Face", "Hope for Haiti or Jumanji", "That's not Pitbull, its Amy Poehler" and "Twitter Questions"
Special guest: Amy Poehler (en)
- Games include: "John Mayer or Pepé Le Pew", "For a Dollar", "Quizzed In the Face", "Who is most famous on Sean Hayes phone", "Actress Potato Head" and "Uninteresting or Uncircumcised"
Special guest: Sean Hayes and Olivia Wilde (en)
- Billy asks Aziz Ansari to pinpoint Kanye West quotes in "Is this a Kanye West Quote or Not?". Rachel Dratch gets plunged into an obstacle course where she must escape Margot Robbie's moment. Also: Aziz and Billy remind New Yorkers that it's the golden age of television in "The Lightning Round", and a tourist plays "James Franco or Real Gay Person?". (en)
- Games include: "Katharine McPhee or Nanny McPhee?", "Lil' Quizzed in the Face", "Smash or Great Gatsby", "For A Dollar" and "It's Debra Messing, You Gays!"
Special guest: Debra Messing and Christian Borle (en)
- Billy heads to Los Angeles to play "Artistic Masterpiece or something Justin Timberlake's Music Reminds Me Of" with James Corden. Later, Billy and James ask people on the streets of Los Angeles to help Billy create his own viral segment in "Curbside Conga Line". Also: Billy encounters a protest against him and his show; "Taraji Jim Henson", and Robin Lord Taylor runs through the "Can You Separate the Art from the Artist" obstacle course. (en)
- Actress Julianna Margulies goes undercover as Sia for a game of "That's not Sia, it's Julianna Margulies!". Billy quizzes Elena and her sister, Edie, about each other. Lucy Liu participates in a game titled "We Have to See What Lucy Liu Thinks". Also: "Kris Jenner or Geppetto". (en)
- Games include: "For A Dollar", "Quizzed in the Face", "Meredith Baxter Birney" and "Joseph Gordon-Levitt Pursuit" (en)
- Games include: "Are You Smarter Than a Gay Fifth Grader?" and "Is this a Real Tyler The Creator Lyric or not?" (en)
- Comedian Seth Rogen guesses his movies based on interpretive dances in "Seth Vogue-en". Later, people give mixed reactions to the news of Seth's death in front of him in "Death Rogen". Also: "What does Michelle Rodriguez Bring to the Table?" and "The Billy on the Street Relay Race". (en)
- Games include: "Where in the world is Scarlett Johanson's Vagina" and "Sho Nuff or no he Didn't" (en)
- Games include: "Quizzed in the Face", "Cash Face" and new game "Indian or not Indian?" (en)
- In a challenge about James Bond stars and cable networks, Billy puts Chris Pratt on the spot. Later, they ask bystanders if they know who Chris is in "The Lightning Round". Also: Quizzed in the Face. (en)
- Billy plays a guessing game about real and faux Macy's Thanksgiving Day Parade moments with Lucy Liu. New Yorkers give thanks to Meg Ryan. Billy hosts his own Thanksgiving Day Parade with Katie Couric. Also: "Mark Twain or Eddie Murphy". (en)
- Lupita Nyong'o joins Billy for a round of "Gay or Old" and plays "Barack Obama or Jennifer Lawrence?", and then hits the street for a special Lightning Round called "Lupita Nyong'o: Bring the Pain". Contestants fumble trying to sing patriotic tunes in "The Patriotic Tunes Lightning Round" featuring Elena. Tituss Burgess sings This Land is Your Land. (en)
- Games include: "For A Dollar", "Amateur Speed Sketching", "Gay or Not a Gay", "Space Craft or Reality Star", "Charlize, Tyrese, or Denise", "Feminine Product or ABC Family?" and "Kathy Bates or Gargamel"
Special guest: Hank Azaria (en)
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