Comedians You Should Know

What Comedians You Should Know does

Comedians You Should Know (CYSK) is a Chicago-based stand-up comedy showcase company founded in 2008. Its flagship offering is a weekly Wednesday live comedy show held in the private 55-seat showroom of Timothy O'Toole's Pub in downtown Chicago, featuring curated selections of Chicago-based and visiting alt and mainstream comedians. Tickets are sold directly to consumers via Eventbrite with no drink minimum requirement. Beyond Chicago, CYSK operates showcases in Los Angeles (since 2015) and New York City (since 2016), making it the only comedian-produced stand-up showcase operating across the three largest U.S. comedy markets.

The company monetizes through three distinct revenue streams: (1) live show ticket sales via Eventbrite, (2) digital comedy album sales through iTunes — having produced 20 albums, several of which reached the top of the iTunes comedy chart, and (3) private event booking fees for college and corporate functions, accessed through a dedicated "Hire Us" contact form. CYSK maintains a content catalog spanning albums by individual comedians such as Ricky Gonzalez, David Drake, and Joe Kilgallon, as well as a self-titled compilation recorded live at one of its shows.

The business operates with approximately 5 employees and is privately held with no disclosed institutional funding, parent company, or M&A activity. Distribution relies on third-party platforms (Eventbrite, iTunes, Gmail) rather than proprietary technology, and the company has no AI/ML capabilities, patents, or proprietary software stack. Marketing is conducted primarily through press coverage (The Onion A.V. Club, Chicago Sun-Times, Laughspin Magazine), an email newsletter, and the company website. Critical acclaim includes a quote from The Onion A.V. Club calling "the genuine quality of talent on display… unrivaled in Chicago."

Name

Comedians You Should Know

Website

https://comediansyoushouldknow.com

Company type

Private

Founded year

2008

Operating status

Operating

Headcount range

1–10 employees

Short description

Comedians You Should Know is a Chicago-based comedy showcase company operating a weekly 55-seat live stand-up show, with satellite showcases in Los Angeles and New York City. It monetizes through ticket sales, iTunes comedy albums, and private event bookings.

Ownership category

akta.pro rank

Product category

Live Comedy Entertainment

NAICS

Theater Companies and Dinner Theaters (71111)

akta.pro primary industry

Comedy Club & Showcase Nights (MPAGACAE)

akta.pro secondary industries

Stand-Up Comedy Shows (MPAGACAA), Comedy Clubs (Nightlife Venues) (MPAGAIAH)

Keywords

• Stand-up comedy showcase
• Live comedy production
• Comedy album sales
• Comedy talent booking
• Live entertainment events

Headquarters

HQ city

Chicago

HQ country

United States

HQ region

North America

Offices3 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Others

Revenue model

1. Live Show Tickets: Ticket sales for weekly Wednesday stand-up comedy showcases at Timothy O'Toole's Pub in Chicago. Seating limited to 55 with no drink minimum.
2. Comedy Albums: Sale of comedy albums through iTunes featuring performances by CYSK comedians. Produced 20 comedy albums, many reaching top of iTunes comedy chart.
3. Private Event Booking: Booking fees for private events at colleges and corporate functions featuring CYSK comedians.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels3 records

Core offering

Comedians You Should Know (CYSK) produces a weekly stand-up comedy showcase featuring top Chicago comedians and visiting performers from both alt and mainstream comedy scenes, held Wednesdays at 8pm in the private showroom of Timothy O'Toole's Pub in downtown Chicago (55-seat capacity, no drink minimum). The company also produces and sells comedy albums on iTunes (20 produced to date) and books its comedians for college and corporate events.

Product overview

Comedians You Should Know (CYSK) is a comedian-produced stand-up comedy showcase company operating primarily in Chicago. The core offering is a weekly live comedy show featuring top Chicago comedians and visiting performers, held at Timothy O'Toole's Pub. The company has expanded to Los Angeles (2015) and New York City (2016). Beyond the live showcase, CYSK produces comedy albums available on iTunes, including albums by Ricky Gonzalez (Kid Stuff), David Drake (Dave), Joe Kilgallon (Pay Attention), and a self-titled debut compilation. The company also offers booking services for corporate events and college performances.

Differentiator

Problem solved

Functional benefit

Products and services

• Weekly Stand-Up Comedy Showcase (CYSK) A weekly stand-up comedy showcase featuring the funniest Chicago comedians and visiting guests from both the alt and mainstream comedy scenes. Held Wednesdays at 8pm in the private showroom of Timothy O'Toole's Pub in downtown Chicago, with seating limited to 55 and no drink minimum. Expanded versions also operate in Los Angeles (since 2015) and New York City (since 2016).
• Private Event Booking (Hire Us) A booking service that arranges CYSK comedians to perform at college events and corporate functions. Inquiries are submitted via a contact form on the website and handled directly by CYSK.
• Comedy Albums (CYSK catalog on iTunes) Comedy albums produced and sold digitally through iTunes, featuring CYSK comedians and live showcase recordings. The catalog includes 20 albums, many reaching the top of the iTunes comedy chart. Documented titles include Ricky Gonzalez - Kid Stuff, David Drake - Dave, Joe Kilgallon - Pay Attention, and the self-titled Comedians You Should Know debut compilation.

Quantifiable outcome

• Produced 20 comedy albums, multiple reaching top of iTunes comedy chart

Segments2 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

One partnership is on record.

• Timothy O'Toole's PubcoreOthers · 1 January 2010Timothy O'Toole's Pub provides the private showroom venue for CYSK's weekly Wednesday shows in downtown Chicago. CYSK relocated from Fizz Bar and Grill in 2010 to this downtown watering hole. The partnership allows CYSK to host their intimate 55-seat comedy showcase.

Scale indicators4 records

Recent moves8 records

Expansion highlights3 records

Broad incumbents

• The Comedy Store: Landmark Los Angeles comedy venue and broader entertainment brand operating in CYSK's LA market with an overlapping comedian-curation model and significantly larger scale.
• The Second City: Chicago-based comedy and improv theater company with a significantly larger scale, training, and touring business, but serving the same live-comedy consumer base in CYSK's home market.
• Laugh Factory: Multi-city comedy club chain with locations including Chicago and LA, offering similar stand-up showcase programming but at a broader, more commercial scale than CYSK.
• The Improv: Established national comedy club chain with weekly stand-up programming across major U.S. cities, competing for the same comedian talent and consumer demand as CYSK.

Direct peers

• Don't Tell Comedy: Pop-up curated stand-up showcase that has expanded across multiple U.S. cities with a similar comedian-produced, ticketed format — the closest direct comparable to CYSK's showcase model.

Regional players

• The Comedy Cellar: Iconic New York City stand-up comedy club operating in CYSK's NYC market with a similar intimate-venue, curated-comedian format.
• iO Theater: Chicago improv and comedy theater operating in CYSK's primary market with a similar venue-based live-comedy model, though weighted toward long-form improv rather than stand-up showcases.
• Helium Comedy Club: Comedy club chain with curated stand-up showcases in multiple U.S. markets, comparable in format (intimate room, ticketed shows) but operating in different geographies than CYSK.
• Zanies Comedy Night Club: Long-running Chicago comedy club with a comparable weekly stand-up calendar and headliner format, operating in the same primary geographic market as CYSK.

Others

• Kill Tony: Long-running live stand-up podcast showcase in Austin that has built a national audience around a weekly live-comedy format; adjacent rather than directly competitive, but draws from and competes for the same touring stand-up talent pool.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat3 records

Key risks5 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/comedians-you-should-know

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Comedians You Should Know