This would be the final season for
Leslie Jones, who had been with the cast for five seasons since 2014. Jones announced her departure on August 27, 2019,[6][7] in favor of focusing on her movie career.
Prior to the start of the season, the show added
Alison Gates, Alan Linic, Eli Mandel, and
Bowen Yang to the writing staff,[4] while co-head writer
Bryan Tucker was designated a senior writer, leaving Colin Jost, Michael Che, and Kent Sublette as the show's remaining head writers.[8] This was the final season for
Katie Rich, who had previously been a writer on the show since
2013.[9]
Following the goodnights, West, wearing a
Make America Great Again hat, went off-script with his support for
Donald Trump. This was discussed in the next episode, during the opening monologue and during the Weekend Update segment.[10]
Wendy Williams appears in the pre-recorded Kyle Mooney film. Additionally, SNL writer and future cast member
Bowen Yang also appears in the same film in a non-speaking role.
"The War in Words" is a new rendition of a sketch from Maya and Marty, with
Mikey Day reprising his role from it.
A short montage of
Dana Carvey imitating
George H. W. Bush, as well as Bush's appearance with Carvey during
season 20, is shown at the end of Weekend Update as a tribute to Bush following his death the night before.
In a break with tradition in which the host introduces the musical guests, Pete Davidson introduces Ronson and Cyrus's second performance. It was Davidson's only live appearance on the show (though he did appear in one pre-recorded sketch). Earlier in the day, a post on Davidson's
Instagram sparked public concern that he was suicidal.[24][25]
This episode attracted negative reactions from Donald Trump, both when the episode originally broadcast, as well as when the episode rebroadcast on March 16, 2019.[26]
Alec Baldwin appears as Donald Trump in the cold open.
John Mulaney appears on Weekend Update with Pete Davidson, who briefly mentions the events from last month when he publicly threatened suicide on Instagram.
The episode's rerun on August 3, 2019 aired the originally Cut for Time "New Cast Member", a short film where Kyle Mooney plays an unknown relative who appears as an unnoticed Saturday Night Live cast member. Also, before the goodnights of this rerun, a photo of former lighting director Phil Hymes was shown. Hymes had died on the Monday of that week.
Chris Rock appears in the opening monologue with Sandler and
Pete Davidson, singing an original song called "I Was Fired".
Jimmy Fallon,
Kristen Wiig, and frequent Sandler collaborator
Allen Covert appear in "Sandler Family Reunion". Additionally, Wiig appears in "Last Call".
Prior to the goodnights, Sandler performs an unplugged musical tribute to
Chris Farley that was originally performed in his 2018 stand-up special Adam Sandler 100% Fresh.
Sandler also does a short impersonation of Farley during the opening monologue.
With this episode, Sandler ties
Dan Aykroyd's record for the longest gap between being a cast member and returning to host the show. The gap for both actors stands at nine days shy of 24 years.[38] Both actors made guest appearances on the show during the time period after leaving the cast and before returning to host. This record was beaten December 21, 2019 by
Eddie Murphy whose gap was 35 years.