The sadder but wiser boy
Lando and Dallas have spent their 20-year co-dependent friendship abusing each other with pranks and insensitivity. Now in their thirties, Dallas takes it upon himself to buy Lando some time with a lady of the night so he can finally "become a man." Over the course of the night, the true nature of the friends' relationship is laid bare, proving that maybe the real friends were the hookers we met along the way.
Directed and Edited by DARYL DELLAWritten by DARYL DELLA & SASHA BOGGSProduced by SASHA BOGGSCinematography by DANIEL CRUZSTARRING:LORENZO OCON as LandoDARYL DELLA as DallasSASHA BOGGS as MistyFEATURING:KAYLA EMERSON as Diner WaitressLORI CARSILLO as Diner Waitress 2RICHARD CASTROMAYOR as TruckerHOLLIS L. EDWARDS III as Burger RecipientKIL THEODRICK as Wet MouthERIC HOWARD, EVAN SANFORD, DOM VERSACI, KIRAN UMAPATHAY, NATÁLIA ALVES as Diner PatronsRAY REVELLO as JayLORI CARSILLO as Lola BombayBENNY NIKOLE as Vegas GirlBRITTANY CAIRO as Cigarette GirlROBERT RUBY, JUSTINE STOUT, GRACIE RHODES, MADELYNN DABBS, LARKIN TEN ELSHOF, BECKER VON FELSBURG, and RYAN FIDLER as Bar PatronsTOM ARNOLD as Roderick FredlinsSETH YAITANES as Detective HickeyTARA ERICKSON as Detective MurphyJONATHAN CAIRO as James AllenWhat People Are Saying
“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…
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.”
— Alan Ng, Film threat
“If you've never spoken the words ‘That really good Tom Arnold film’ then here's your chance! ”
— Screaming Ostrich Film Festival
“In Daryl Della‘s compelling short comedy drama, co-written with Sasha Boggs, the toxic undercurrents of a life-long friendship take center stage, unraveling a narrative that goes beyond laughter into the realms of insecurity, co-dependency, and self-discovery…
Della’s drama crafts a moving and comical journey that seamlessly balances humor with a poignant exploration of loneliness, sexuality, and the consequences of toxic friendships. The high-quality cinematography by Daniel Cruz enhances the visual appeal, complementing the terrific acting performances.
Despite its comedic elements, the film transcends the genre, leaving the audience with a real message about the importance of self-worth and the detrimental effects of toxic relationships. Della’s work stands as a testament to the potential of comedy to deliver powerful and thought-provoking narratives.”
— short films matter
awards and festivals
complete your collection with the sadder but wiser boy on blu-ray
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• Outtakes
• Original Trailer
• “Real Boy” Music Video - David Quintanilla feat. Lorenzo Ocon & Sasha Boggs
• Crime Squad: Pervert Division - Full scene starring Tom Arnold
• 2022 Premiere Event Promo - Trailer for Dollars & Donuts last Bay Area premiere
• Dollars & Donuts Is Dead. Long Live Dollars & Donuts! - Intro to the 2022 Premiere
• Still Walking (2015) - Remastered short film
• Jumping Jacks with “Weird Al” Yankovic (2015)
• “Pretenzo” Music Video (2009) - Remastered from the original tapes
• 2015 Vegas trip - Footage from the trip that inspired parts of the film
• Fear & Lozo In Las Vegas - Previously unreleased LozoTV video, (too hot for Youtube!) featuring another film-inspiring trip to Las Vegas
• Life with Lozo - Unreleased LozoTV video
• Lozo 'R' Us - Another classic LozoTV video
Original trailer
The charming true-life adventures of two lifelong co-dependent friends who won't stop abusing each other. Now in their thirties, Dallas (Daryl Della) decides it's time to help Lando (Lorenzo Ocon) finally become a man. Nothing like Rain Man or The 40-Year-Old Virgin at all!
“Real Boy” Music Video
david quintanilla ft. lorenzo ocon & sasha boggs
From the Soundtrack to Dollars & Donuts' The Sadder but Wiser Boy
Produced by Mad Sounds Productions
Characters
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Dallas
DARYL DELLA
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Lando
LORENZO OCON
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Misty
SASHA BOGGS
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Roderick Fredlins
TOM ARNOLD
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Lola Bombay
LORI CARSILLO
behind the scenes
Director’s statement
The Sadder but Wiser Boy is more than a comedic short film; it's an intimate peek into a two-decade-long friendship between me and my buddy Lorenzo. While some of the escapades may seem too insane to be real, I assure you, they happened.
Lando and Dallas, while exaggerated for the screen, echo the essence of our dynamic – navigating a sea of pranks, screaming matches, and those unbelievable (and maybe regrettable) moments. Through this film, I sought not only to entertain but also to reflect, utilizing the camera as both a mirror and a magnifying glass.
In presenting The Sadder but Wiser Boy, I offer not just a piece of cinema, but a piece of my own life, raw and unvarnished. It's a confessional in the guise of fiction, a testament to the beautiful absurdity of the ups, downs, and sideways of a friendship that's lasted way longer than it maybe should have.
Daryl Henry Della
