Comedy Writing – With Oliver Long

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Professional Comedy Writing

“Comedy writing is finding humor in the most unexpected places—sometimes it’s the serious topics that hide the best punchlines.”

Oliver Long has established himself as one of the industry’s most sought-after contracted comedy writers, blending sharp wit with meticulous research to create humor that resonates across audiences. With over a decade of experience crafting comedy for various clients, Oliver has developed a unique approach to finding humor in both everyday situations and complex topics.

His journey began with early creative experiments—much like many comedy writers who start by exploring different artistic outlets before finding their true calling. “I was always drawn to creating things that made people laugh,” Oliver explains. “It’s about finding that perfect balance between the relatable and the surprising.”

THE CRAFT OF COMEDY WRITING

Oliver’s writing process combines structure with spontaneity. He typically begins by identifying a topic with comedic potential, then explores the emotions and images surrounding it—a technique similar to what many professional comedians employ. For Oliver, the contrast between ordinary and extraordinary is where the magic happens.

“One comedy concept to be aware of is that if your topic is ‘weird,’ it will be most effective if you place it in an ordinary backdrop. Alternatively, if the issue is bland and representative of everyday life, land it in the most unusual and bizarre setting,” he notes, echoing a principle that has guided his successful career.

Unlike stand-up comedy where a joke might be just four words long, contracted comedy writing requires developing extended narratives while maintaining humor throughout. Oliver excels at this long-form approach, creating comedy that sustains interest while delivering consistent laughs.

RESEARCH AND RELEVANCE

What sets Oliver apart in the industry is his commitment to thorough research. “In general, it is just a rigorously researched comedy show: both because we want it to be right, and for self-preservation purposes,” he explains of his process, which mirrors the approach used by successful comedy shows.

This research-driven methodology allows Oliver to find humor in serious topics that might not initially seem funny. “There are funny things about how entrenched some of those problems are,” he observes. “And sometimes I think comedy is the best, most illuminating way to talk about them”.

THE BUSINESS OF BEING FUNNY

Building a contracted comedy writing business requires more than just being funny—it demands professionalism, versatility, and business acumen. Oliver has cultivated relationships with diverse clients while maintaining his distinctive voice, a balance that many creative professionals struggle to achieve.

His DIY approach and what he calls a “punk attitude” toward comedy writing have allowed him to maintain creative independence while meeting client needs. This philosophy has helped him navigate the business aspects of comedy writing without compromising his artistic integrity.

Oliver’s success demonstrates that comedy writing can be both a creative outlet and a sustainable career path, offering inspiration to aspiring writers looking to turn their humor into a profession.

The Writer’s Life Series features in-depth conversations with professionals who have turned their passion for writing into successful careers. Each volume explores the creative process, business insights, and personal journeys of these remarkable individuals.

Contact:

If you would like to contact Oliver Long about his comedy writing experience, for now, visit our CONTACT page and fill out the form.  That will email me, and I will relay the message.

We protect our customer’s privacy, and unless otherwise noted, protect our interviewee & subject’s privacy with the same vigor.

Comedy Writing Questions Answered:

Oliver Long comedy writing business:

Career Background and Establishment

• How did you first discover your talent for comedy writing, and what motivated you to turn it into a professional service?
• Can you walk us through the early days of establishing your contracted comedy writing business? What were some of the initial challenges you faced?
• What was your first big break or client that made you realize this could be a sustainable career path?
• How has your comedy writing style evolved over the decade you’ve been in business?

Creative Process and Inspiration

• Where do you typically draw inspiration for your comedy writing? Are there particular experiences, people, or sources that consistently fuel your creativity?
• Can you describe your typical process when approaching a new comedy writing project for a client?
• How do you handle writer’s block or creative dry spells when you’re on a deadline?
• Comedy is often described as subjective. How do you navigate writing humor that will resonate with different audiences or client specifications?

Industry Insights and Credibility

• What credentials or accomplishments have helped establish your credibility in the comedy writing industry?
• How do you stay current with comedy trends while maintaining your unique voice?
• What types of clients or projects do you typically work with, and how has your client base evolved over time?
• What’s been your most challenging project to date, and how did you overcome those challenges?

Business Aspects

• How do you approach pricing your services in an industry where creative value can be difficult to quantify?
• What marketing strategies have been most effective for growing your contracted comedy writing business?
• How do you balance the business side with the creative aspects of your work?

Career Opportunities and Future Outlook

• What unexpected doors or opportunities has your comedy writing career opened for you?
• How do you see the field of contracted comedy writing evolving in the next five years?
• Are there adjacent industries or career paths that comedy writers might explore to diversify their opportunities?

Advice for Aspiring Comedy Writers

• What skills or qualities do you believe are essential for someone looking to break into professional comedy writing?
• What advice would you give to someone who wants to start their own contracted comedy writing service?
• Looking back on your journey, what do you know now that you wish you’d known when you first started?

 

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