Ed Bailey is at a good place in life.

The 31-year-old comedian lives happily with his long-time girlfriend, Khamil, and their two young children. He co-hosts a monthly comedy showcase at the Comtra Theatre, co-hosts one of Pittsburgh’s most popular podcasts, Drinking Partners, and will have his very first headlining gig at the Pittsburgh Improv this Wednesday, May 17.

All great reasons to be happy, for sure, but his contentedness is colored by near-tragedy: on January 21, Bailey was returning from a comedy show in Ohio when his car was struck and flipped by a tractor-trailer.

His life nearly ended.


“This is the most positive I’ve felt, which is so crazy because it’s after something so terrible,” he says. “When you almost die, you really just appreciate being alive. At the end of the day, you know you don’t have to be here. You don’t have to be able to see your mom, your sister, your kids.”

He spent weeks sedated, breathing only with the aid of a ventilator. His doctors feared permanent brain damage. Bailey has no memory of the accident or even the week leading up to it.

“I went to sleep, Obama was president. I woke up, Trump was President and the Patriots had won the Super Bowl.”

“I’m scared to go back to sleep now,” he says, flashing an understated grin.

Asked about his injuries, he recites them with the nonchalance of a person ticking items off a grocery list. “I had a collapsed lung, and my other lung was badly bruised. I broke my scapula. I broke my ulna, so now the fingers on my left hand can’t close all the way. I broke several vertebrae up and down my spine, so I have weird shit going on with my neck and my nerves. I think that’s it.”

“Didn’t you break a bunch of ribs, too?”

“Oh, and I broke 13 ribs. I forgot about them.”



Ed Bailey III grew up in East Cleveland, Ohio. He was an introverted child, one who would act silly and joke among friends but not the type who wanted to be the center of attention.

He grew up as a big Martin Lawrence fanhe remembers watching ComicView late at night with the volume turned low so his mom couldn’t hearbut he never really considered becoming a comedian until later in life simply because, growing up, comedy never seemed like a legitimate career.

Bailey moved to Pittsburgh to study finance at Pitt and has been here ever since. He worked a 9-to-5 job after college (he still works in retail banking) until his girlfriend encouraged him to pursue standup at the age of 27.

His first public performance was at a regular open mic at Pleasure Bar called Comedy Sauce, hosted by Aaron Kleiber.

“He looked like a seasoned comic, and I asked him how long he had done comedy for in Cleveland,” recalls Kleiber. “He looked like he’d been doing comedy for two years at that point and it was his first time.”

Bailey stood out from the beginning for his poise, dynamic storytelling, and ability to find new angles on well-worn themes, says local comedian, T-Robe, who was on-hand for Ed’s first set at the Pittsburgh Improv.

“Ed was so calm,” he recalls. “I’ve been doing comedy for 16 years. I’ve been on tour with Dave Chappelle, so for him to impress me with just a couple months under his belt, I told him, look, if you’re serious about this you can go real far.”

Bailey quickly became a regular at open mic nights around town and it didn’t take long for others to take notice as well.

One story goes like this: comedian Hannibal Buress, after headlining a set at Mr. Smalls, swung by Hambone’s for open mic night. Bailey, not even six months into his standup career, so impressed Buress that he invited Bailey to open for him with a 20- minute set in Cleveland the very next night.

“It was great,” remembers Bailey, “but I didn’t have 20 minutes, dude. I did about seven strong and forced the other 13.”

Bailey says that his style of comedy, generally speaking, is that of a “hip, urban, cool dad,” someone who still kicks it with friends but comes home to a house with young kids. (His daughter is three years old; his son, nine months.)

“That’s a perspective that is undersold in comedy,” he says. “Generally, ‘Dad comics’ are older comics. I think that’s why Kevin Hart is successful with his bits about his kids. Most of the parents with small children are late 20s/early 30s. Do you want to hear a 52-year-old comic saying, ‘Kids! They spill things!’ or a 30-year-old saying, ‘Man, I came home from the bar and my daughter was still awake, so now I have to deal with my daughter drunk.’”

“It’s just real stuff that I talk about. Everybody can relate.”

Brian Conway

Brian Conway is a writer and photographer whose articles have appeared in the Chicago Tribune and local publications. In his free time, he operates Tripsburgh. Brian lives in the South Side.