This Day in Country History: February 14

Breakthrough Hits and Milestones

• 1977: Jimmy Buffett releases one of his most recognizable hits, "Margaritaville." The song would reach No. 1 on Adult Contemporary, No. 8 on the Hot 100 charts, and No. 13 on Hot Country songs.
• 2006: “Boondocks” by Little Big Town was certified as a gold single. It would later go on to be 3x Platinum certified.
• 2006: A remake of "Cowboys Are Frequently, Secretly Fond of Each Other" by Willie Nelson is released.
• 2021: Blake Shelton and Brad Paisley co-hosted the NBC TV special, Grand Ole Opry: 95 Years Of Country Music. This two-hour special showcased some of the Opry's key performances, superstars, and up-and-coming country music stars. Performers included Kelsea Ballerini, Carrie Underwood, Dierks Bentley, and Kane Brown. 
• 2022: Billboard released its list of the greatest love songs for couples to listen to for their Valentine's Day celebrations. Songs included were Rascal Flatts's "Bless the Broken Road," Keith Urban's "Making Memories of Us," and Kacey Musgraves' "Butterflies."

Cultural Milestones

• 1939: Razzy Bailey was born in Alabama. He had six consecutive hits in the early 1980s.
• 1997: Ty England and wife welcome their third child, Levi Wyatt.
• 1998: Hal Ketchum married his third wife, Gina Pacconi, in Austin, Texas.
• 2001: Emily Robison from Dixie Chicks appeared on the celebrity version of Who Wants To Be A Millionaire?
• 2010: Taylor Swift debuted in the movie Valentine's Day.
• 2016: Joey Floyd from Toby Keith's Easy Money Band passed away. Floyd played guitar, fiddle, and banjo for the band and, as a youngster, acted in a movie with Willie Nelson.
• 2021: The Country Music Hall of Fame and Museum closed its long-running exhibit Outlaws & Armadillos: Country's Roaring '70s, which opened on May 25, 2018. This exhibit highlighted the careers of country music outlaw legends such as Willie Nelson, Waylon Jennings, Billy Joe Shaver, and Jessi Colter. 
• 2025: SNL celebrated its 50th Anniversary show with a star-studded lineup. Performers and entertainers who appeared on this iconic show included Bonnie Raitt, Brandi Carlile, Miley Cyrus, Jelly Roll, and Lady Gaga. Many of the stars took a moment to remember late SNL cast members like Gilda Radner and John Belushi.

Notable Recordings and Performances

• 1974: Bob Dylan performs with The Band in Los Angeles. Those in attendance included Warren Beatty, Ringo Starr, and Neil Young.
• 1977: Dolly Parton launched her 18th solo studio album, New Harvest...First Gathering. This was her first self-produced album.
• 1985: Randy Travis signed a Warner Bros. contract two weeks after recording “On The Other Hand.” The song reached No. 1 on the country charts.
• 2021: Garth Brooks' album Triple Live received a 4x Platinum certification from the Recording Industry Association of America (RIAA). In addition, Fresh Horses had gotten an 8x Platinum certification, and No Fences received an 18x Platinum certification on this date.

Industry Changes and Challenges

• 1997: The "Should've Asked Her Faster" singer, Tyler England, and his wife, Shanna, welcome a baby boy, Levi Wyatt, on this day. Levi was welcomed by his sister, Aspen, and brother, Christian Tyler.
• 2018: The widow of the late Troy Gentry, Angela Gentry, filed a lawsuit against Sikorsky Aircraft Corp., Sikorsky Global Helicopters, and Keystone Helicopter Corp. in the death of her husband. Gentry, part of the duo Montgomery Gentry, was killed in a helicopter crash on Sept. 8, 2017, in New Jersey.