Jessica Michelle Singleton

Jessica Michelle Singleton

Everyone has been hurt by COVID, but literally, no sub-population has been hit harder more figuratively than stand-up comics.

With no release valve for the pent up neurosis and dysfunction that makes a person funny, these souls have had to find new outlets to express themselves and get the attention and adulation they necessarily crave. Jessica Michelle Singleton, who is probably the most successful female comic to ever come out of Anchorage, has used her hiatus to produce something quite novel — a country song titled ‘Now I Need Whiskey’, available on Amazon, and pretty much any music streaming app.

When I spoke with her last month, she was prepping for a comedy show that night at the Rose Bowl, which, if for a second you forgot about the pandemic, sounds awfully impressive. Even Dane Cook in his prime couldn’t fill up a 92,000-seat football stadium, but alas, the pandemic is never far from our consciousness and Singleton’s show was indeed in the parking lot of the Rose Bowl. 

Drive-in parking lot shows have been about the best alternatives to stage shows most comics could hope for, but unfortunately for Singleton, a city of Pasadena noise ordinance prohibits honking as an alternative expression of laughter.

“It’s the biggest show I’ve ever done — not to oversell it,” Singleton joked. “It’s been dead-silent, very silent since the venues shut down… But I have my first weekend booked in Sacramento at the end of April and I’m looking at Anchorage at the end of the summer, so it’s going well. Thankfully, things are starting to pick back up.”

Singleton said years of karaoke and a professional musician for a hunker down buddy spawned the idea for cutting the song.

“I kind of did it on a whim. It’s a bucket list thing. I always wanted to write a country song,” she said. “My experience is mostly as a drunk-ass, obnoxious karaoke queen. I lived in Anchorage from middle school through high school and before that I was in Jackson, Mississippi so those are two cities with a good country music scene.”

The Service High grad and homecoming queen said she discovered her karaoke chops when she went to college in Florida.

“I tried out for American Idol four times — did the cattle calls,” Singleton said. “Country was always the music I kind of liked — those cheeky Johnny Cash songs, a lot of songs about running from the law or cocaine blues. In the mainstream, I like Miranda Lambert, getting wild, getting into trouble, but I also get into sappy heartwrenching country… I’ve always kind of liked that sense of humor — giving the finger to whoever.”

Singleton also appreciated country music’s feminist roots, which, it could be argued, are decades ahead of stand-up comedy. While female comics today can still be considered shocking for talking bluntly about the enjoyment of sex, 40 years ago Tammy Wynette and Loretta Lynn were smashing the patriarchy with anthems like ‘D-I-V-O-R-C-E’ and ‘The Pill’.

“If you go back to Lucinda Williams or Loretta Lynn — their songs were very not dirty like my song is, more like ‘bless your heart/sleep with my man and I’ll beat the crap out of you,’” Singleton said. “It’s about a woman making it big in any industry, not taking crap from anybody and sticking up for themselves. It is a feminist sort of thing.”

To help her write and produce the song, Singleton leaned on her boyfriend Andy Warren, who is also the drummer for the popular alt-rock band The Mowglis.

“He could understand the sound I was trying to go for. I don’t know anything about the technical side — I can barely play a guitar,” Singleton said. “If he were doing comedy I’d would say, ‘OK, I’ll help you do comedy,’ so when I asked him about it he was like, ‘well, I guess you show me your boobs sometimes so I have to help you a little.’”

‘Now I Need a Whiskey’ opens with the presumably quasi-autobiographical line:

‘I heard ‘Friends in Low Places’ when my daddy left me in a Waffle House in Jackson, Mississippi…’ as a defense in the affirmative for the character who experiences adulthood as a progressively worsening violent criminal, first punching out her boss, the next day killing her boss, being sentenced to 50 years in prison, beating up her cellmate and celebrating it all with an old outlaw country song brought to mind, a smoke break, and, of course, that desperately needed whiskey.

The single has been quite well received in social media circles, enough to encourage Singleton to put together an EP before spring is out.

“We didn’t want to overestimate assumptions. I have an audience built in that knows me for comedy, but maybe they would be into it or not… but people have been getting really excited about it,” she said. “We’re still getting the bones (of an EP) together, more heavily leaning into the same lane of outlaw country. It may even get a little grittier, touch on drugs and get a little wild with it.”

Singleton said she’s even considering a very serious song about drug addiction inspired by the recent death of a friend.

“Anchorage has a bit of a drug problem and a lot of friends of mine went down a dark path,” she said. “I want to try to tap into the shame and struggle of it all. About a week before we dropped this song, a buddy I grew up singing with at the top of our lungs in an old Ford Ranger passed away.”

Whatever comes of the EP, Singleton now undoubtedly has the opportunity to be a double-threat performer, an opportunity she’s begun to explore.

“I’m now talking to some people — industry management people and there’s a country singer out of Texas named Rich O’Toole, who’s in the outlaw country scene who wants me to come open for him,” Singleton said. “I said, ‘sure, I have one song,’ but I’m looking at making a trip to Nashville and setting up some type of music; find a way to mix (music and comedy).”

Singleton said she’s hoping to make it back to Anchorage sometime in August to do a show at Koots. Like all comics, she’s wrestled with the issue of how much of COVID and the lockdowns to put in her act.

“For me, comedy is about my own fears and anxiety… I want to forget about this shit,” she said. “People come to the show to get away from all the stressful stuff and I think my job as a comedian is to take people’s mind off of the bad stuff.”

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