Comedy
There is no shortage of standup that takes the raw material of hapless, disappointing life and turns it into laughter. That’s a sizable part of what comedy does. But for big, big laughter fashioned from pretty severe instances of disappointment, look no further than James Acaster’s career-best 2018 show, Cold Lasagne Hate Myself 1999. It takes two low moments in the Kettering man’s life (being dumped by his girlfriend in favour of, er, Mr Bean; and being dumped by his agent after an on-air PR gaffe) and – in two hours of gasp-inducing, gut-bustingly funny standup – recasts those disappointments as mere staging posts on the route to comedy glory. Brian Logan
TV
Disappointment hangs over Betty Suarez, the Latina titular character of Ugly Betty, like a sword of Damocles, waiting for the moment to finally tear her apart. The series begins with her disenchanted: her job as an assistant at Mode magazine is unglamorous, and her colleagues are visibly displeased at being forced to accommodate her poncho, braces and sanguine confidence – attributes that are “unchic” in the world of mid-2000s high fashion. It makes for ironic viewing now: transplant Betty into the 2020s and you can imagine her with a viral Instagram account focused on thrifting and sustainability; Mode’s cruel receptionist Amanda, the apparent embodiment of the 00s “it girl”, would be left behind in her wake. Jason Okundaye
Music
Very few bands convert sadness into elegance quite like Radiohead. Although Thom Yorke’s writing often revolves round menacing, downtrodden critiques of consumerist culture, the chorus of Kid A’s Optimistic makes use of one uplifting mantra: “You try the best you can / You try the best you can / The best you can is good enough”. At times of self-doubt, my partner often recites this chorus to me, temporarily accepting its meaning independently from the song. It’s a simple phrasing, but a welcome reminder nonetheless that in life and lyricism, we have to learn from our failures. Jenessa Williams
Books
Eleven-year-old Luke Parker’s knowledge of comics is encyclopedic. Costumes, symbols, abilities, origins – he’s a superhero savant. This makes it still more galling that while he nips off for a wee, his maths-obsessed older brother Zack is given superpowers by a visiting alien. Luke’s jealous disappointment, coupled with his determination to mentor Zack (or at least get him wearing a cape), shapes David Solomons’s hilarious novel My Brother Is a Superhero, full of fraying fraternal bonds and a mission to save not one, but two worlds that will need all Luke’s knowhow – as well as Zack’s powers – to succeed. Imogen Russell Williams
Film
In the 1949 film The Heiress, Catherine (Olivia de Havilland), a wealthy but dowdy disappointment to her autocratic father, falls hard for Morris (Montgomery Clift), who in turn disappoints her. William Wyler’s gripping melodrama is a dazzling depiction of disillusion, providing De Havilland with an extraordinary, Oscar-winning role, in which she adjusts the wick on her natural luminosity like it’s a gas lamp that can bathe the room in brightness or make shadows leap large across the wall. The sorrow of the underestimated, unloved soul pervades the film but Catherine’s final act of vengeful disdain makes it also the cruellest success story, as a wilting wallflower comes to know her intrinsic self-worth as never before. Jessica Kiang