1. The Fire Incident

Before Jennifer Aniston could present her first award of the night, Jimmy Kimmel thought it would be best to walk her through disinfecting an envelope. Little did he know that alcohol-based sanitizer was flammable. He throws the envelope in the trash can and sets it aflame only for it to create a small raging fire. Thankfully Aniston was there to extinguish it, but not without a fight. She repeatedly put it out multiple times until it finally dulled out. 

2. Cardboard Cutout 

As the awards ceremony opened, many familiar faces greeted us, but none of them were real. Unfortunately, these were only cardboard cutouts and not the real actors and actresses. However, you’d be surprised to know that James Bateman joined Kimmel at the Emmys, pretending to be a cardboard cutout among the many in the audience. 

3. USPS Skit 

Later in the ceremony, Anthony Carrigan appears on stage dressed as a USPS mailman. Kimmel and Carrigan perform a skit poking fun at the USPS controversy with a mailman spoof. The act features Carrigan as a Russian mailman who asks Kimmel for his ballot and promises that it is safe with him. 

4. Union’s rap

Gabrielle Union introduces Issa Rae’s HBO series “Insecure” for the outstanding comedy series category by performing a hilarious rap. Her husband Dwyane Wade also appears in the video. 

5. When you lose the Emmy

After Eugene Levy won the Emmy for lead actor in a comedy series, Ramy Youssef shared a hilarious video with the caption “when you lose the Emmy,” revealing a clip of an award presenter wearing a hazmat suit and waving from outside of his house. The presenter then takes away the golden trophy.