Entertainment Music Country Jenna Paulette Authentically Depicts Heartbreak in 'Pretty Ugly' Video: 'Sometimes Things Can Be Both' Jenna Paulette enlists a family friend to star in her ranch-set new music video about how heartbreak makes pretty ugly By Cindy Watts Cindy Watts Instagram Twitter Cindy Watts is a CMA Award-winning journalist who has spent more than 20 years reporting on country music from Nashville, Tennessee. The bulk of her career was spent with The USA Today Network. She has a degree in recording industry from Middle Tennessee State University, where she recently spent a semester teaching journalism. She currently co-hosts 52-The Podcast alongside Sugarland singer/songwriter Kristian Bush. She adores baking, The Golden Girls and Dolly Parton, but not as much as she loves her two children. People Editorial Guidelines Published on September 15, 2021 11:00 AM Share Tweet Pin Email Jenna Paulette was familiar with the pretty ugly song idea. Her friend Jeb Gipson had pitched her the song title many times, but she couldn't figure out where it was headed. When the pair had a co-write with Parker Welling and Will Bundy, Welling's unique spin on the concept piqued Paulette's interest. "She was like, 'What if it's heartbreak that makes pretty ugly?" Paulette recalls. "I was like, 'That's so good." "Pretty Ugly" is Paulette's new single and the focus of her new music video that costars family friend Eli Dangelmayr. PEOPLE has the exclusive premiere of the video, which explores the honest side of love gone wrong. "I wanted the ugly stuff to be stuff that you go through when you are stressed, and you are going through something, whether it's smoking and drinking or eating Twinkies," she says. "That's just our [coping] mechanisms in life. I think it was important to show the stark contrast between when things are good and when they aren't. It drives the hook home." Jenna Paulette. Nick Swift For the video, Paulette wanted to use real cowboys. She enlisted not only Dangelmayr but also the use of his family's ranch in Muenster, Texas. Since she grew up working on her family's ranch in Oklahoma, authentically depicting the lifestyle and its people was essential to her. Paulette knew other ranchers would spot an imposter a mile away, and she was careful to ensure her video was believable. She created a "Pure Country" vibe in reference to George Strait's popular cowboy movie — complete with a man wearing a straw and a pearl snap shirt with a woman who was oblivious to any problems. The rancher even let them carve their initials in the tree for the video — a symbol of forever. At the end, when the on-screen relationship didn't unfold as expected, she planned to chop the tree down. "For that to be the thread throughout the whole video was really fun for me," she explains. The song is a classic turn of phrase, with lyrics including: "Mascara running down a made-up face / Clouds rolled in now it always rains / It was beautiful up until he said he didn't love me / Heartbreak makes pretty ugly." "We just went to town on the juxtaposition of pretty and ugly and how things can be going so good, and then all of a sudden they aren't what you thought they were," she says. "It can be anything. It doesn't have to be a relationship." Jenna Paulette. Nick Swift Paulette's sister recently found out she has breast cancer. The diagnosis made the singer realize that ruined relationships aren't the only situations that can flip life from pretty to ugly. "You get a call that takes you from pretty to ugly in a couple of words," she says. "It was a timely thing, but the easiest way to tell the story was through a break-up lens."