Laughing Out Loud

Comedian Megan Gailey has built a Hollywood career out of her biting wit and hilariously unfiltered storytelling. Funny thing is, she gets some of her best material back home in Indiana.
Photo courtesy Andrew Lipovsky

HER PINSTRIPED BLAZER, a silver lamé number with matching shorts, shimmers against the famous cobalt-blue curtain on the set of The Tonight Show Starring Jimmy Fallon. In this light and with her signature full-face smile, Megan Gailey looks as if she is actually glowing. She could be a disco queen, an old-Hollywood starlet, or the captain of a girls’ night out in Broad Ripple, all roles that fall well within the range of this Indianapolis-born, Los Angeles-based comedian, writer, and actor whose star is on the rise.

But in the clip from Fallon, a YouTube video with a 2019 timestamp, Gailey riffs on being a childless aunt, among “the scariest people alive,” she tells the audience—imagine a woman whose screensaver is a baby she didn’t give birth to. She also jokes about her then-recent engagement by way of a “surprise” proposal in Indy beneath the Michigan Street mural of her longtime hero, former Pacer Reggie Miller—an event that was covered in The Indianapolis Star alongside her original Tweet, “I guess you can make a hoe a housewife,” and blessed by the NBA legend himself with a “BOOMBABY” in the comments. She says she knew her fiance (sports creative agency owner and fellow screenwriter C.J. Toledano) was up to something, because he asked for her dad’s phone number. That, and the fact that she had already designed her own engagement ring. “He proposed to me in a shirt that said ‘Mount Dunkmore.’ Do you think he knows rose gold looks good on potato famine skin? I don’t think so,” she says. When Gailey’s four minutes and 30 seconds are up, Fallon rushes over to shake her hand, shouting over the applause, “Oh, my gosh. Oh. My. Gosh. Potato famine skin! Megan Gailey! That’s how you do it.”

How does she do it, exactly? The Lawrence Central High School grad who grew up in the Geist area and majored in theater and communications at Purdue University has made a career of zigging where you think she’s going to zag. Since her earliest days in the business, showing up for open mic nights around Indianapolis, Bloomington, and Muncie in her early 20s, Gailey has spiked her wholesome Midwestern charm with unbridled, blush-inducing raunch. She is, in the words of her own standup script, an outspoken “Karen for good” with “resting Confederacy face” who speaks with an unapologetic sorority-girl vocal fry that is “the voice Black teenagers use to make fun of white women.” She gets it. She owns it. She weaponizes the fact that she definitely looks “like someone who has yelled at a Panera before,” and then she spins the narrative on its ear. Not only is Gailey in on the joke, but she will beat you to the punchline.

Photo courtesy Isaac Poole

At some point between the intro and the mic drop, she will mention that she hails from Indiana—a Hoosier to her Ranch dressing core. It’s just that she’s not the kind of Hoosier her audience thinks they’re getting.

Gailey’s appearance on Fallon might have been one of her biggest breakout moments, but a lot has happened since then. This includes a wedding in Palm Springs that was covered by The Cut, a global pandemic, a baby boy named Conrad, a new house in Los Angeles, multiple writing gigs, and a monthslong Writers Guild of America strike during which she was able to focus on her first passion: stand-up. In addition to filling her calendar with local shows and tours, Gailey co-hosted the I Love a Lifetime Movie podcast with fellow comedian Naomi Ekperigin. Last year, it received a Best Comedy Podcast nomination for The Ambies—the Academy Awards of podcasts. She wrote for the HBO comedy series Pause With Sam Jay, and she created and sold three television pilots, each one with an Indiana tie-in, of course.

Gailey currently shares hilariously relatable tales of parenting (but absolutely no parenting advice, she guarantees) alongside dad comics Kurt Braunohler and Chris Garcia on the I Love My Kid, But … podcast. Their weekly dispatch is described as a judgment-free “safe place for parents to get away from it all,” with episode titles that range from “My House Looks Like Someone Robbed the Double Dare Set,” to “It’s Like Living With Your Worst Internet Trolls,” to “We All Don’t Fight in the Bounce House!” In nearly every installment, Gailey slips in a reference to her own upper-middle-class childhood. Her dad, Geoff Gailey, is a retired HR executive who worked for companies such as Fisher Price Toys, Solo Cup, and Indianapolis Power & Light. Her mom, Peggy Gailey, is a former nurse who also taught high school career courses. She grew up with two older brothers, one of whom once dialed 911 in an attempt to get himself ungrounded, an anecdote that illustrates the podcast’s tone and thesis that parenting is—and always has been—more akin to the Wild West than polite society.

Photo courtesy Mandee Johnson

The Gailey family remains very close-knit, still vacationing together en masse with their spouses and children and attending Pacers and Colts games when they’re all in town. “It is my dream,” Gailey says, “for my entire family to sing the National Anthem at one of the home games.”

That’s not such a stretch. Gailey herself is an avid sports fan who knows her way around the X’s and O’s. She used to work for the NFL, has written for the ESPYs, and remains the kind of home team devotee who receives promotional merch from marketing departments. In an unboxing video on Instagram, she threw on a Rik Smits T-shirt before opening the package that contained her personalized Pacers Nike City Edition team jersey as her toddler son (whose middle name is Jalen, as in Jalen Rose) adorably cheered her on. She was under the RCA Dome for the 2007 AFC Championship game when the Colts finally beat the New England Patriots to advance to the Super Bowl. She considered it the greatest day of her life, a proud moment in Indianapolis history that she and her brother witnessed from their family seats seven rows above the field. The celebration afterwards was so sweet, they both cried happy tears.

Gailey spreads the Indiana sportsball gospel via comedic yet spot-on NFL video previews and on sports-centric podcasts such as The Greatest, NBA Storyline, and All Fantasy Everything. She takes her self-appointed job as the one-woman West Coast PR bureau for Indy sports seriously, recently posting on the X platform, “I cannot overstate how great it is for Indy’s morale and economics for the Pacers and Colts to be positive news stories right now. Both of those teams play in gorgeous stadiums downtown and downtown Indy needs this boost!”

Photo courtesy Megan Gailey

But Gailey’s Hoosier enthusiasm extends beyond sports. She’s known to show some twisted pride as a regular guest on a long list of comedy podcasts hosted by her colleagues in entertainment. When she mentioned on the LGBTQ-focused You’re Making It Worse that she hails from Indianapolis, one of the hosts declared the reveal “such a fun curveball.” On Do You Need a Ride, she discussed her parents’ neighbor and good friend, Tom Griswold of The Bob & Tom Show. She shared the spooky legend of the flooded town at the bottom of Geist reservoir on the paranormal Ghosted! By Roz Hernandez. And on the Los Angeles–based podcast Mall Talk (which is exactly what it sounds like), she waxed poetic about the “heaven on earth” that is The Fashion Mall at Keystone at the Crossing, with its art house movie theater, department store piano player, and dearly departed Talbots Kids shop, where she would get an adorable new birthday outfit every year.

She’s only joking when she calls it the Los Angeles of Indiana, but you have to admit, Megan Gailey’s Indianapolis sounds like a pretty cool place.

THE 2004 Lawrence Central class president and 2003 Junior Prom Queen is in the process of planning her 20-year class reunion. “I off-loaded my 10-year,” Gailey says. “But this year, they’re like, ‘You need to do this.’ … Do people still like to go out in Broad Ripple?”

Gailey frets over this task as she wraps her hands around a massive pastrami sandwich at Shapiro’s Delicatessen. It’s the Saturday after Thanksgiving, midway through a six-day trip back home with her husband and son, and so far, they have eaten turkey dinner with the family, attended a Pacers game, hung out with her best friend since childhood, and hit the Slippery Noodle. Last night, they saw a movie, where she was recognized by a fan. “My mom tells me I need a social assistant when I come home to visit. There are always places I want to go to and people I’d like to see while I’m here, so it’s never very relaxing.”

Photography by Jes Nijjer

Gailey has loaded her tray with potato pancakes, asparagus spears, and a massive double-decker wedge of carrot cake on the bottom combined with cheesecake on top. Clearly, she has done this before. In fact, Shapiro’s has always been one of her favorite spots in town. Her family has been coming here since she was a little girl, an experience so special to her that she picked the bustling downtown landmark as the location for her third grade birthday party. It was an odd choice for a child, but not an unusual one for a child whose parents are transplanted New York professionals who wanted to get the most out of their adopted hometown. Peggy Gailey remembers how all the birthday partygoers’ little eyes glazed over when they saw the cafeteria line. “I said, ‘OK, how about each of you pick out three things?’ So we ate, and then we went duckpin bowling at Iaria’s.”

“A lot of the things we did socially with the kids were downtown,” adds Geoff Gailey. There were trips to the Children’s Museum, meals at the L.S. Ayres Tea Room, and special occasions at The Columbia Club. It’s no wonder their only daughter, who grew up to record a 2019 comedy album titled My Dad Paid for This, would glean comedy gold from such an enchanted childhood.

As with most comedy, though, there is a touch of darkness if you read closely between the punchlines. One of Gailey’s earliest sets includes a series of stories about her father’s struggles with alcohol. There’s a joke about how he passed out during the Super Bowl one year … even though he was a big football fan … and he was at the Super Bowl. “That’s kind of a $10,000 oopsie,” she deadpanned during her appearance on The Tonight Show With Conan O’Brien in 2015, which was the first time her father heard the joke.

Photo courtesy Megan Gailey

“It’s a true story, sadly,” Geoff Gailey says. “And so, I’ve been working on my sobriety with some success, which she celebrates, as all of us do. There are some people who might say that’s not really fit for public consumption. But under the heading of support—it got a laugh.” He maintains that this brand of unconditional support for his daughter’s art encouraged her to create freely.

But it’s tricky maneuvering through a life laid so bare for laughs. Gailey knows this. Considering that a joke she told about her dad when she was 23 has stuck with him for years, she wonders—worries, even—that someday her son might resent his role in her comedy. She co-hosts a podcast about parenting called I Love My Kid, But …, for heaven’s sake. And that little guy is an endless source of material. But … “It’s one of my biggest fears. I think about it constantly—what is Conrad going to talk about in therapy?” Gailey says.

It’s much easier to think about a different trajectory in which Conrad, like his mom, gets the joke and runs with it. He already knows how to hold a karaoke microphone up to his mouth like a seasoned stand-up comic. Maybe comedy is in his blood, too. If it is, imagine the stories he will tell.