In the fifth and final season of sitcom Hacks, the legendary comedian Deborah Vance has once again been plunged into crisis. After leaving America’s number one late-night talkshow in a flurry of controversy, a vengeful non-compete clause is barring her from performing new material. Season four of the Emmy-winning comedy ended on a cliffhanger, with TMZ mistakenly reporting that Deborah (Jean Smart) had died. Freshly resurrected for season five, the prodigal mother of comedy worries that her lifetime of work will be defined by her premature late-night exit. To secure her legacy, she sets her sights on staging a major comeback show at Madison Square Garden – and she’ll stop at nothing to make it happen.

Not uncoincidentally, the final season of The Comeback begins on a similar note of desperation. Valerie Cherish – the high-cringe sitcom star played by a red-haired Lisa Kudrow – is handed a career lifeline when she scores the lead role in a new sitcom. There’s just one catch: the script has been written by AI, and this is a secret that Valerie is forbidden from sharing. It’s the type of toe-curling scenario that could only come from Kudrow and her collaborator, Michael Patrick King, who is back on form after terrorising the world with And Just Like That.

There is a satisfying symmetry to these shows – two HBO sitcoms starring women over 60, which are ostensibly about the painstaking process of making people laugh – airing their final seasons concurrently. Both shows illuminate a cultural habit of projecting “comeback” narratives on to women who feel society’s pressure to constantly reinvent themselves to have their greatness celebrated. And they also mock the indignities of fame today, where we seem to force even the most iconic stars to chase relevance and clicks. In these shows, the demands of algorithm-era fame are the bleakest – and funniest – punchline.

Last season on Hacks, when Deborah became the host of late night, we saw how quickly her talent was dimmed by external pressures. In pursuit of ratings, her guests included the fictional TikTok star Dance Mom, and she was forced to practically stalk an unsuspecting Kristen Bell around an LA market to beg her to appear. The commercial demands of the network put Deborah on an endless merry-go-round of filming TikToks and social clips, shaking hands at parties, and doing just about everything apart from what made her famous: comedy. Two episodes into season five, we’ve already seen her rallying her fans (the “Little Debbies”) at a convention with a blue-painted Ann Dowd, and we’ll soon see her dancing while dressed in a clown costume.

I sensed a similar bleakness in The Moment – the Charli xcx “mockumentary” that followed the star as her onscreen avatar tried to draw a line under Brat summer. Charli had succeeded in coloring the zeitgeist radioactive green, but the mechanisms around her seemed determined to erase her creativity from her work, subjecting her to a grueling schedule of product launches and brand promo, including her very own Brat credit card. She began to chase “viral” social media moments, despite knowing that it was all throwaway nonsense. As Charli spent hours being stitched into a skin-tight dress to film a short clip where she shared the insides of her purse, I felt myself yearning for the era where celebrities were more distant, untouchable figures, and where we didn’t feel entitled to have such access to them.

In both Hacks and The Comeback, the protagonists are cornerstones of old-school celebrity, before the arrival of reality stars and influencers. Yet even women like them, with a craft and a legacy, are still judged by the attention economy of today, where if people stop talking about you for five minutes you might as well not exist. That’s why, in this season of The Comeback, we see Valerie trying (and failing) to master the dumbed down “Real Housewives version” of Chicago on Broadway. We also learn that she went mega-viral on The Traitors – for being totally useless, of course. And now, as she records her own sitcom (and a docuseries about making the sitcom) her aptly named social intern, Patience, scurries around after her trying to record clips. It’s no longer enough to have a craft: you have to make more and more content to stay relevant.

In fact, the whole premise of The Comeback is Valerie trying to cling on to her cultural value by leaning into new forms of media – first reality TV and now AI. But underneath it all, what she really wants is to be taken seriously as a comedy actor. Similarly, in the season five premiere of Hacks, Deborah develops a sudden obsession with achieving Egot (Emmy, Grammy, Oscar, Tony) status, which sees her record a music album in Spanish in the hope of snagging a Grammy. Ava reminds her that her legacy won’t be defined by award statistics or publicity stunts. “You are going to be remembered for comedy,” she says, “because you’re a comedian.”

As a culture, we seem to be addicted to projecting comeback narratives on to even the most talented women. In their own HBO-created worlds, Deborah and Valerie are of a different status. (Deborah is already a formidable icon when we meet her, while Valerie’s position always seems more precarious.) Yet in their final chapter, they feel more aligned. By this point, both women have survived decades in an industry that is still obsessed with the newest thing and, despite their many awards, achievements and respective reinventions, it never feels like enough. The goalposts keep moving and they’re always one failure away from being declared a flop.

I noticed something similar on my social feed when Madonna announced her long-awaited return with Confessions II. At first, I even felt myself projecting a sense of all-or-nothing on to her return – as if everything rode on the album being a hit, despite her 2024 Celebration tour concluding with the biggest crowd of her career in Rio de Janeiro. But I realised that my kneejerk response was contributing, in real time, to the type of expectations that Taylor Swift described in her 2020 Netflix documentary, Miss Americana. “The female artists that I know of have to remake themselves 20 times more than the male artists,” Swift said. “Or else you’re out of a job.” The truth is that Madonna could release an album of fart sounds set to dance beats and she would still be the queen of pop.

In the season premiere of Hacks, as Deborah chases yet another reinvention, she stages a secret gig to try out some new material after being silenced by the non-compete clause. “When you’re away from the spotlight, you have time to think about what really matters …” she says, before answering her own question: “The spotlight!” These shows reveal the extreme, undignified lengths that Deborah and Valerie are willing to go in order to stage the perfect comeback story one more time. But should they have to?

• Hacks and The Comeback are on HBO Max