Monroe County Fair performers Jackson Dean, Caitlyn Smith rising in country music circles

Fast-rising country singers Jackson Dean and Caitlyn Smith, who will perform Aug. 5 at the Monroe County Fair, are quickly climbing country music charts.

Dean is earning a reputation for his old-school, gritty, lyric-driven, outlaw style of country, according to his website.

This follows a breakout year that landed him on Pandora’s Ten for 2023 list, Spotify’s Hot Country Artists to Watch 2023, the CMT Listen Up class of 2023, CRS New Faces 2023, Amazon Music’s 2023 Breakthrough Artists to Watch Country Class as well as a slew of other “artist to watch” lists.

More: Tickets to see concerts, grandstand shows at Monroe County Fair go on sale

Jackson, a Maryland native, opted to move out to a cinderblock, concrete floor, one-room shack on the back of his grandfather’s property with no heat and no plumbing at just 18 years old. Today, the 22-year-old multi-instrumentalist is also an artisan whose pastimes include making leather goods and wood-burned art.

His debut album, “Greenbroke,” was released through Big Machine Records. His single “Don’t Come Lookin’” was the fastest debut song to reach No. 1 in 2022 and made Jackson the youngest solo male country artist to reach the top of the charts with a debut. He also produced songs that landed with spots on the Billboard Hot 100, the soundtrack for Netflix’s “The Ice Road” and a John Dutton scene in “Yellowstone.”

His second single, “Fearless (The Echo),” is currently climbing the country radio charts after being named “Most Added.”

Following an early career of local performances in his hometown, Jackson now performs with acts such as Toby Keith, Miranda Lambert, Brantley Gilbert, Kane Brown, Jake Owen, Brooks & Dunn, Lee Brice, Hardy and Brothers Osborne. He recently kicked off the “Back to the Honky Tonk Tour” with Blake Shelton and Carly Pearce and will join dates with Eric Church and Parker McCollum later this year.

Caitlyn Smith was raised in Cannon Falls, Minnesota, and was named one of Rolling Stone Magazine's "10 New Artists You Need To Know.”

After releasing her hit single “High” through Monument Records, Forbes magazine called the song “captivating,” and The Tennessean newspaper said the song “showcases an artist finally in control of her life and career," according to her website.

In April, Smith released her complete album project, adding six new songs to the track. For Smith, 36, the making of “High & Low” represented a “metamorphosis,” the website stated.

The additional five new tracks from “High” were celebrated by National Public Radio as “her most fully realized project yet, with ‘High & Low’ capturing the full picture of who Smith is as an artist and as a creator – where embracing the yin and yang simply makes you more human.”

Other hit songs for her include “Lately,” “Mississippi,” “Starfire,” “Long Time Coming” and “Maybe in Another Life.” She also recorded "The Card You Gamble," the theme song of the drama series “Monarch,” which premiered in 2022.

Smith’s debut album, “Starfire” was released through Monument Records in 2018 and was followed by her second studio album, “Supernova,” in 2020.

She has written songs recorded by Meghan Trainor ("Like I'm Gonna Lose You," a duet with John Legend that rose to No. 1 on Billboard Adult Top 40 chart), Kenny Rogers and Dolly Parton ("You Can't Make Old Friends"), Avicii ("Chained") and Miley Cyrus ("High").

Smith has played at Lollapalooza, Bourbon & Beyond Festival, Americana Fest and ACL Fest.

Looking back, the award-winning songwriter and musician graced the pages of both “Time” magazine and The New York Times and was named Paste’s 10 country artists to watch.

Smith has also spent the past few years on the road opening for George Strait, Reba McEntire, Little Big Town and Old Dominion. That led to her debut on “The Kelly Clarkson Show.” She’s also performed on “Late Night with Seth Meyers,” “The Tonight Show Starring Jimmy Fallon,” “The Today Show” and “CBS This Morning.”

Last year, Smith headlined her “High & Low” tour and headed overseas to perform as part of C2C in London.

This article originally appeared on The Monroe News: Monroe County Fair performers Jackson Dean, Caitlyn Smith rising