The Sadder but Wiser Boy Image

The Sadder but Wiser Boy

By Alan Ng | April 26, 2023

The thing about friends is they’re there during the best and worst of times. Unfortunately, in the case of writer Sasha Boggs and co-writer/director Daryl Della’s comedy short, The Sadder But Wiser Boy, friends are often the cause of the best and mostly worst of times. The friends in question are Dallas (Daryl Della) and Lando (Lorenzo Ocon).

Lando is the uptight one of the crew, and Dallas thrives on busting Lando’s balls. On this day, Dallas promised to pay for Lando to lose his virginity to his hooker friend, Misty (Sasha Boggs). Having no money of his own, Orlando has to pay Dallas back with jumping jacks.

“Dallas promised to pay for Lando to lose his virginity to his hooker friend…”

The Sadder But Wiser Boy is about this very dysfunctional friendship. There’s an odd sweetness between the two leads. Lando always seems to be always walking on the edge of insanity, and Dallas takes an odd pleasure in keeping him on edge. Dallas knows how to press buttons, and Lando is helpless to act in any other way than through frustrated anger. The question then becomes how much longer can Dallas keep doing this?

The short falls squarely in the cringe comedy category. In his attempt to lose his virginity, Lando is pushed to his most vulnerable moment while Dallas is pulling the strings. Though the plot may be cringe, the laughs come in the small moments with the jumping jacks and the combative nature between the friends.

While writing this review, I’m looking back at just how frustratingly fun The Sadder but Wiser Boy is. Dallas is horrible to Lando. Lando’s sadsack personality constantly foils any good that can come to his life. Yet, I’m oddly drawn to this maladjusted friendship, like watching a freeway pileup. Maybe I’m sticking with this tale to see how it unfolds or falls apart down the road.

For screening information about The Sadder but Wiser Boy, visit the Dollars & Donuts Productions official website.

The Sadder but Wiser Boy (2023)

Directed: Daryl Della

Written: Daryl Della, Sasha Boggs

Starring: Lorenzo Ocon, Daryl Della, Sasha Boggs, etc.

Movie score: 8.5/10

The Sadder but Wiser Boy Image

"…falls squarely in the cringe comedy category."

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