Skyler Gisondo

In Booksmart (2019), Jared has the confidence of a rich boy and a sweetness that makes it difficult to dismiss him. Gisondo gets the comedy out of that combination without treating the character as disposable once the joke has landed. We warmed to Jared more than we expected, because Gisondo keeps his earnestness visible beneath the overconfidence. Olivia Wilde's high-school comedy gives that skill a useful setting: it is interested in young people who have overestimated their judgement. The film tidies up its central friends' mistakes too neatly, but its warmth suits an actor who can make an over-the-top supporting character endearing.

Vacation (2015), with Gisondo as James Griswold, sits in the earlier stretch of supporting film roles. Booksmart brought wider attention, followed by his appearance as Lance Brannigan in Paul Thomas Anderson's Licorice Pizza (2021). There was also the sustained work of playing Gideon Gemstone in Danny McBride's The Righteous Gemstones (2019–2025). These parts have made good use of his suitability for ensembles. The danger is that being dependable in a familiar sort of part gives casting directors little reason to ask for anything else.

James Gunn's Superman (2025) shows the limits of that suitability. Gisondo plays Jimmy Olsen, the Daily Planet photographer, and his affability makes the casting easy to understand. But Jimmy's subplot belongs in a sillier film, and Gisondo's presence cannot make it fit the one around it. We found the film kind and bright but too busy, with its accumulating characters and crises eventually becoming noise. That is a problem with what he has been given to do; it tells us little about what a more demanding part might bring out of him.

The quality we would like to see tested further is his ability to let vulnerability show through the comedy. Sweetness can become bland if a film asks for nothing else, but Jared's overconfidence gives Gisondo something awkward to work with. Wilde gets more from that combination than Gunn's crowded film allows, and it is the collaboration we would point to first. Start with Booksmart; he is worth watching when a film lets him be foolish as well as nice.