Saturday Night Live host Jake Gyllenhaal went through a maze of Southwest employees–and one Hudson News cashier, mistakenly–all in an effort to simply cancel his flight.
While being transferred to nearly ten different people, Gyllenhaal encountered customer service representatives who mispronounced his name all sorts of ways, those with odd racial views, those who demanded something in return, and unreasonably long and indecipherable audio-only confirmation codes, among other things.
Gyllenhaal ultimately was transferred by a trainee (Devon Walker) to a Hudson News cashier (Andrew Dismukes), before being reconnected with his original contact at Southwest (Mikey Day). Moments later, Gyllenhaal spoke with “the highest ranking Southwest employee.”
Bowen Yang, dressed in Native American-esque garb with Southwest’s colors, responded to his request from what looked like another dimension. Yang ultimately granted it–but not before mandating a cancelling fee and rebooking charge.
Gyllenhaal, who previously hosted SNL in 2022 and 2007, teamed up with Dismukes in another sketch where he plays the soon-to-be father-in-law of the SNL cast member.
In the sketch, Gyllenhaal demands absolute discretion from Dismukes after he eats a cookie after his wife just told him not to. The Road House star goes on to make Dismukes’ proposal to his daughter much more complicated than it needed to be.
Michaela Coel in ‘The Christophers.’Claudette Barius/NEON
