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- S5.E1 ∙ Kevin Bacon Wears a Blue Button Down Shirt and Brown Boots
- S5.E2 ∙ The Lonely Island Wear Dark Pants and Eyeglasses
- S5.E3 ∙ Tony Hale Wears a Blue Flannel Shirt and Fuchsia Sneakers
- S5.E4 ∙ Tegan and Sara Wear Leather Jackets and Skinny Jeans
- S5.E5 ∙ T-Pain Wears Shredded Jeans and a Printed Shirt
- S5.E6 ∙ Aubrey Plaza Wears a Velvet Off-the-Shoulder Gown with Flowers in Her Hair
- S5.E7 ∙ Joe Jonas Wears a Maroon and Gold Letterman Jacket with White Sneakers
- S5.E8 ∙ Nathan Fielder Wears a Blue and Grey Flannel and Jeans
- S5.E9 ∙ Kristen Schaal Wears Strawberry Colored Pants and a Multicolored Shirt
- S5.E10 ∙ Zach Galifianakis Wears Rolled Khakis and Shoes with Brown Laces
- S5.E11 ∙ Kaley Cuoco Wears a Black Blazer and Slip on Sneakers
- S5.E12 ∙ Gillian Jacobs Wears a Gray Checkered Suit and a Red Bow Tie
- S5.E13 ∙ Scott Aukerman Wears a Tailored Black Suit
- S5.E14 ∙ Krysten Ritter Wears a Turtleneck and Black Boots
- S5.E15 ∙ Allison Janney Wears a Chambray Western Shirt and Suede Fringe Boots
- S5.E16 ∙ Ben Folds Wears a Black Button Down and Jeans
- S5.E17 ∙ Malin Akerman Wears a Black Blouse and Cropped Jeans
- S5.E18 ∙ Mike Colter Wears a Pink Button Up and Black Boots
- S5.E19 ∙ Reggie Watts Wears a Purple and Yellow Quilted Sweatshirt
- S5.E20 ∙ Lord Andrew Lloyd Webber Wears a Purple Top Hat & Fabrice Fabrice Wears One Pink Fur Leg Warmer