If you asked 2011 graduate Jessie Ritter to recall some of her most memorable performances from high school, singing Taylor Swift’s “Fifteen” to an incoming freshman class in Notre Dame’s gymnasium would be somewhere on that list. Less than a decade later would Ritter land a deal with the same record label as the famed pop singer, and not only be performing original songs on stages along the Gulf Coast, but over the air across the country.

It’s All About Taking The Risk

Notre Dame was the “perfect starting point” for Ritter. As a senior, she organized the school’s annual benefit concert, which gave her insight to the music business world she hoped to pursue post-graduation. Being cast as the lead in the dance-heavy spring musical Thoroughly Modern Millie in 2010 also showed her that as a performer, you’re always learning something new.

“I’ve not tap-danced since then, but it’s that aspect of trying something that I didn’t think I could do,” said Ritter. “And taking a risk onstage… that I still do all the time.”

When it came time for college, she had a choice to make. Medical school was sort of a tradition in her family, and a career in music has its challenges. But, according to Ritter, music “just gets in your blood.”

“I knew that I had to give it a shot, and I had to tell myself that I’d just do it until it didn’t work anymore. Just see what we can make happen. The fact that I have made it work like this is such a big blessing,” she said.

She went on to attend Belmont University in Nashville where she majored in commercial music. Six weeks after graduating in 2015, life was uncertain. The lease on her apartment was up, her roommates were leaving, and things were at a standstill. That is, until she got a call from Carnival Cruise Lines.

“They asked ‘Do you want to live on a ship? Sail six nights a week around the Bahamas and get paid every two weeks? I was like… yes,” said Ritter. “My roommate called it an ‘organized adventure.’ I’d get to travel and meet new people, but I was on a schedule, knew when I would get paid, and knew where I needed to be. It was the perfect combination.”

Ahoy, Full-Time Music Career!

When she boarded the boat, Ritter was in for a two-year gig. She worked four hours a night, six nights a week for entertainment-hungry travelers. She sang everything from Motown to disco, from soul to classic rock, gaining the necessary versatility for the career ahead of her.

“It greatly expanded my musical repertoire, but also it banished all stage fright. Because when you have to do it all week, it’s your job,” said Ritter. “When you go to work, you can’t be nervous about it, because this is where you have to be.”

The unfamiliar genres weren’t the only diversity Ritter had to acquaint herself with: as an international company, Carnival hires performers from all over the world.

“Our guitar player was from England. Our drummer was from Colombia,” said Ritter. “And when you’re working with a Colombian drummer, you’ve got rhythms in there that you would never have if you had an American band full of 20-year-old white boys. That was an opportunity I would’ve never gotten if I hadn’t worked in this niche of a music community.”

She started on a ship in the Bahamas, as promised, but was later assigned to ships on other seas.

“I was moved to Australia, and got to see all that part of the world, and then they sent me on the Europe ship. I got to go from Barcelona to Athens and back,” said Ritter. “Then we sailed a brand new ship into NYC.”

After her return to the states, Ritter finally felt she had gotten the best of what these itineraries had to offer. She had traveled, explored, and widened her skill set, but was ready to sing her own songs; to become “more of the artist, not just the musician.”

The Girl In The Pink Hat

Ritter, again, had to decide where she would plant herself. The three contenders were Cape Girardeau, the bustling music city of Nashville, and Florida, where her boyfriend (now husband) Brian Toups called home. She chose the latter; not just for Toups, but for the career possibilities.

“I knew there was a lot of entertainment on the Gulf Coast, just like on the ship where we’d been playing for people on vacation who wanted to go to the beach, hang out, and listen to music at night,” said Ritter. “It’s really the same thing, but it’s just on land.”

This made for an easy transition. She was hired instantly by a rock band because she knew all of the songs, already had great costumes, and was well-prepared. She booked more clubs and venues as word spread, and eventually evolved back to her solo show.

“I’m mostly playing my songs on my own, which is really cool. Now I’ve worked up to playing my songs with a full band again,” said Ritter. “It’s kind of a 360-degree morph of the music.”

At the end of July 2018, Ritter unveiled her first full-length album, Coffee Every Morning. It wasn’t too long before strangers started requesting original songs during her sets.

“Maybe they’re a friend of a friend or maybe they actually have heard it on the radio, but it’s really neat to see people I don’t know singing along,” said Ritter. “It’s this once-removed effect of touching people with your music.”

Shortly after the release, Ritter entered one of the album’s songs – Meet Your Mother – in Nash Next, a talent competition offering the chance to land a recording contract and airplay on Cumulus Media affiliate stations. She won the Fort Walton Beach division of the contest, and after another judging round, was one of ten selected from 52 preliminary winners across the country to compete in the live finals in Nashville.

When it came time for her performance, Ritter said it wasn’t a question of who was going to do great and who was going to mess up; it was about who the label was looking for.

“Do they want the tough country dude who wears leather jackets and rides motorcycles and smokes cigarettes? Or do they want the little girl who writes love songs and wears lace dresses and pink hats?” said Ritter. “Apparently, they went for the pink-hat girl that night, because we ended up winning the whole thing!”

She signed a deal with Big Machine Records – the label home of big-name stars such as Florida Georgia Line, Rascal Flatts, Brett Young, Brantley Gilbert, Reba McIntire, and Ritter’s idol, Taylor Swift.

“I should be like “Oh my gosh, I got a record deal,” but what I’m really thinking is ‘I’m on the same label as Taylor Swift!” she said.

This win was the first in a string of many Ritter would experience over the next year. In October 2018, she opened for Easton Corbin, a country music artist she’d once seen perform at the Show-Me-Center in Cape Girardeau as a 17-year-old. In May of this year, she released her first collaborative single with Big Machine called “Nothing But You,” which has since been gathering national radio play.

In June, she played her biggest show to date when she opened for Hunter Hayes – and a crowd of 10,000 people – at the Pensacola Navy Base. She also made an appearance in Cape Girardeau for the outdoor concert series Tunes at Twilight, and has played countless shows along the Florida panhandle.

“I can reach so much of the country staying here. It’s like a reverse tour where they come to me instead of me going there,” said Ritter. “That’s the best little niche of this area that wouldn’t happen anywhere else. I can play the same venue six nights a week and everybody in town rotates.”

While the big venues are exciting for her, she still appreciates the small set, the humble lugging of equipment from gig to gig, and the occasional songwriter’s night.

“It’s like when I played the Pensacola Songwriters Festival, and I got to sit and play onstage with people who have written number-one hits for people like Tim McGraw,” she said. “And, you know, the one-hour Jessie shows are what I like best.”

Now, Ritter is looking to expand to places like Louisiana, Alabama, Georgia, other cities in Tennessee, and will hopefully make a run through the Carolinas next spring. She currently has a new batch of songs awaiting release, and she can’t wait to share them.