Private Project

The Sadder but Wiser Boy

Lando (Lorenzo Ocon) and Dallas (Daryl Della) have been inseparable for two decades, but their friendship has been marked by an endless cycle of pranks and hurtful comments. As they enter their thirties, Dallas decides to help Lando lose his virginity by arranging for him to spend time with a prostitute named Misty (Sasha Boggs) in San Francisco.

When they meet Misty to discuss the details, Lando feels pressured to share stories about his past failed attempts to lose his virginity. As Lando and Misty retire to a hotel room to consummate their arrangement, they unexpectedly bond over their shared regrets and disappointments. Meanwhile, Dallas is left alone at the bar, where he receives a stern lecture from his bartender friend Jay (Ray Revello) about his bullying behavior. Dallas is forced to confront the true nature of his relationship with Lando and the toll their toxic dynamic has taken on both of them.

Throughout the course of the night, Dallas and Lando’s true selves are revealed, proving that maybe the real friends were the hookers we met along the way.

  • Daryl Henry Della
    Director
    A Lust for Time, Am I See You?, Night Dicks: Miami, The Tattoo
  • Daryl Della
    Writer
  • Sasha Boggs
    Writer
  • Sasha Boggs
    Producer
  • Daryl Della
    Producer
  • Daniel Cruz
    Cinematography
    Shadows in the Snow, After the Jack
  • Lorenzo Ocon
    Key Cast
    "Lando"
  • Daryl Della
    Key Cast
    "Dallas"
  • Sasha Boggs
    Key Cast
    "Misty"
    Am I See You?, The Tattoo, Night Dicks: Miami
  • Ray Revello
    Key Cast
    "Jay"
    Am I See You?, Shadows in the Snow
  • Tom Arnold
    Key Cast
    "Roderick Fredlins"
    True Lies, The Stupids, Night Dicks: Miami
  • Kayla Emerson
    Key Cast
    "Diner Waitress"
  • Richard Castromayor
    Key Cast
    "Trucker"
    Night Dicks: Miami
  • Benny Nikole
    Key Cast
    "Vegas Girl"
  • Seth Yaitanes
    Key Cast
    "Detective Hickey"
  • Tara Erickson
    Key Cast
    "Detective Murphy"
  • Project Type:
    Short
  • Genres:
    Drama, Comedy
  • Runtime:
    29 minutes 26 seconds
  • Completion Date:
    December 1, 2022
  • Production Budget:
    10,000 USD
  • Country of Origin:
    United States
  • Country of Filming:
    United States
  • Language:
    English
  • Shooting Format:
    Digital
  • Aspect Ratio:
    2.35
  • Film Color:
    Color
  • First-time Filmmaker:
    No
  • Student Project:
    No
  • Digital Cinema Package:
    Unavailable
  • White Vulture Film Festival
    Hawthorne, New Jersey
    United States
    Best Comedy Short, Best Director- Daryl Della, Best Supporting Actor - Daryl Della
Director Biography - Daryl Henry Della

Daryl Della has been making films for 20 years, amassing an impressive filmography of shorts. He founded Dollars & Donuts Productions in 2003 and has been the de facto director and editor for nearly all the films they’ve created. He has recently stepped in front of the camera for the first time, winning an award for Best Supporting Actor from the White Vulture Film Festival for his performance in The Sadder but Wiser Boy.

Add Director Biography
Director Statement

"The Sadder but Wiser Boy" is more than a comedic short film; it's an intimate dive into the tapestry of a two-decade-long friendship between me and my buddy Lorenzo. While some of the escapades seem straight out of a wild comedy sketch, they're authentically plucked from our real-life adventures.

Lando and Dallas, while exaggerated for the screen, echo the essence of our dynamic – navigating a sea of pranks, gaffes, and those "you-can’t-make-this-stuff-up" 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.