Watch the New Comedy Central Pilot “Lucky Loser” With Big Jay Oakerson Now


Big Jay Oakerson has a brand new digital Pilot available on Comedy Central to watch. In the series, titled “Lucky Loser with Big Jay Oakerson” Big Jay plays a kind of street smart cupid, helping bring together those who are looking for love, and can’t find it. Here’s how Jay describes his role in the Pilot, titled Natalia and Skip.
“In my act I do a lot of crowdwork,” Jay says, “within that crowd work I’ve become known for hooking up couples. So I decided to see if I can take my matchmaking skills pro, and become a champion to underdogs everywhere.”
So Jay takes Natalia, who is desperate to find love, and hooks her up with old college friend “Skip” who is waiting poolside on a rooftop with refreshments. Watch the whole six minute episode on Comedy Central now and see if Jay’s bow and arrow finds love for Skip and Natalia.
“Lucky Loser” is created by Mark Farrell and Sansan Fibri with Mile High Entertainment and directed by Mark. Mark and Sansan are currently working on a documentary about legendary comedian Patrice O’Neal.
Here’s how it works.
Step One: Jay Meets Natalia. Natalia is a self proclaimed Loser.

Step Two: Jay Introduces Natalia to Skip

Step Three: Jay Introduces Natalia to Skips Friends

Step Four: The Moment of Truth: Hotel Room? Or Blurred Out Metro Card?

Sometimes Cupid has a nose ring. @BigJayOakerson brings love to the loveless in Lucky Loser. http://t.co/nmeAs2bvKt pic.twitter.com/XGsb0Gwhfr
— Comedy Central (@ComedyCentral) September 21, 2015
