When Shawn Mendes’ Appearance on ‘The Tonight Show’ Got Embarrassing Because He Called Jimmy Fallon 'Old'

After becoming a household celebrity on Saturday Night Live, Jimmy Fallon launched a new chapter in his career by presenting The Tonight Show. This meant that many celebrities were making their first appearances on his show (when they were still not known as well as today). While Fallon has conducted many entertaining interviews over the years, there have been a few celebs whose initial appearances on his show were less than stellar. Shawn Mendes was among them, and he received an uncomfortably subdued response from the audience after making a remark about Fallon's age, as per The Things.

Shawn Mendes originally appeared on The Tonight Show in 2016, assisting Fallon with a #FallSongs segment. Mendes performed a part in which he sang other people's tweets. Mendes' first tweet was set to the rhythm of his hit, Stitches. However, things became a little awkward when Mendes sang the second tweet.

Mendes seemed to be upset with the second song, saying that it was Fallon who gave him a late cue, making his rendition of Sound of Silence (set to the user's tweet) a bit off. This prompted Mendes to crack a few jokes about Fallon's age. At first, the audience was laughing, but when Mendes stated, "You sound like my grandfather," the room became silent.

Mendes made an effort to continue their playful exchange, but it wasn't very endearing because the singer essentially simply kept making fun of Jimmy for being old. When several of Mendes' 'burns' eventually failed to land with the audience, Fallon continued to play along at first but allowed Mendes to experience some awkward silences.

This was only the first time Mendes was on the show, but Fallon was not angry about this exchange. He would later share the stage with the Treat You Better singer multiple times. In fact, the singer and Fallon shared another awkward yet entertaining moment in 2018. Mendes mentioned appearing at the 2018 iHeartRadio Music Festival alongside Justin Timberlake. Since his time on Saturday Night Live, Fallon and Timberlake have maintained a very open friendship. Owing to their close and long friendship, Fallon started making fun of Mendes for 'liking' Timberlake more. Timberlake and Mendes, he retorted, are 'pretty good friends now.' However, as the conversation went on, spectators appeared to feel the interaction was becoming increasingly awkward.

The two actually were in perfect sync when, in 2022, Mendes and Fallon co-hosted The Tonight Show's April 29 episode. Mendes initially appeared during the opening monologue, dressed in the same black suit and slim tie as Fallon, supporting the comedian-turned-host with wisecracks about electric buses in New York City and irritating alarm clocks. The two then participated in the 'Thank You Notes' segment and the 'Egg Russian Roulette.'

Mendes changed into a light brown jacket later on in the program and sat next to Fallon at the desk for a discussion with Modern Family actor Jesse Tyler Ferguson. After that, the performer sat down for a customary interview with Fallon.