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Demotivational Guru Meets Globe-trotting Comedian in Hilarious New Show: “An Evening with Masood Boomgaard and Self-Help Singh”
(March 2025) – The master of brutal honesty and comedic enlightenment is back! South African comedian Masood Boomgaard returns to the United States with his brand-new live experience, “An Evening with Masood Boomgaard and Self-Help Singh”—a unique double dose of hilarity, wisdom, and wonderfully unapologetic real talk.
Best known as the mind behind the viral sensation Self-Help Singh, Masood has built a cult following around the world with his deadpan delivery, mock-spiritual guidance, and soul-crushingly honest advice. The Self-Help Singh character is a satirical take on the over-saturated self-help industry, offering painfully funny truths instead of feel-good fluff. Think Deepak Chopra if he had zero interest in your success.
Now, in this new two-in-one comedy experience, fans will get more than just the Singh persona. For the first time on a U.S. stage, audiences will also meet the real Masood Boomgaard—comedian, world traveler, and man behind the madness. Masood will pull back the curtain to share stories from his life, his upbringing in South Africa, and his journey performing stand-up across more than o20 countries. Expect sharp insights, hilarious cultural commentary, and behind-the-scenes tales from a career built on turning awkward truths into comedy gold.
This is more than a comedy show—it’s a demotivational awakening with a deeply personal twist.
Whether you’re a long-time disciple of Self-Help Singh or just someone who enjoys a good laugh at the absurdity of life, An Evening with Masood Boomgaard and Self-Help Singh promises a night of enlightenment, entertainment, and existential despair in the best way possible.
The Den Theatre and comedy club is pleased to host AN EVENING WITH MASOOD BOOMGAARD & SELF-HELP SINGH on July 13, 2025 at 1331 N. Milwaukee Ave. in Chicago’s Wicker Park neighborhood.
Tickets are currently available at thedentheatre.com or by calling (773) 697-3830.
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