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10 of the biggest country singers with the longest careers

Talia Lakritz   

10 of the biggest country singers with the longest careers
Willie Nelson and Dolly Parton have dominated the country music scene for decades.Jason Davis/Getty Images for SiriusXM, David Crotty/Contributor/Getty Images
  • Loretta Lynn released her 45th studio album, "Wouldn't It Be Great," in 2018.
  • Since 1967, Dolly Parton has won eight Grammy awards, as well as a Grammy Lifetime Achievement Award.
  • Tim McGraw and Faith Hill are a country music power couple who have been making hits together since the 1990s.

There's a reason country stars like Loretta Lynn, Dolly Parton, Garth Brooks, and Alan Jackson have enjoyed careers spanning decades. Their soulful voices and vivid storytelling have defined and transformed country music throughout the 20th and 21st centuries.

Here are 10 singers who continue to dominate the country music scene.

Loretta Lynn signed her first record deal in 1960 and found success with her debut single, "I'm a Honky Tonk Girl."

Loretta Lynn signed her first record deal in 1960 and found success with her debut single, "I
Loretta Lynn performs at the Grand Ole Opry in the 1960s.      Getty Images

With bold songs like "You Ain't Woman Enough," and "Don't Come Home a-Drinkin' (with Lovin' on Your Mind)," and "The Pill," Lynn cemented herself as a feminist icon and paved the way for more women to sing empowering country anthems. In 1972, she was also the first woman to win CMA's Entertainer of the Year award.

Lynn has received many prestigious honors over her career, including Kennedy Center Honors, a Grammy Lifetime Achievement Award, CMT's Artist of a Lifetime, and the Presidential Medal of Freedom.

Lynn has received many prestigious honors over her career, including Kennedy Center Honors, a Grammy Lifetime Achievement Award, CMT
Loretta Lynn in 2017.      Rich Fury/ AP

Lynn stepped back from public life after having a stroke in 2017, but still released her 45th studio album, "Wouldn't It Be Great," in 2018.

Willie Nelson's first album was called "And Then I Wrote." He released it in 1962.

Willie Nelson
Willie Nelson in 1978.      AP

Before he released his own music, Nelson wrote hit songs for other artists such as Ray Price, Patsy Cline, Faron Young, and Billy Walker. He won his first Grammy in 1975.

Nelson was inducted into the Country Music Hall of Fame in 1993.

Nelson was inducted into the Country Music Hall of Fame in 1993.
Willie Nelson today.      Jason Davis/Getty Images for SiriusXM

In addition to 10 Grammy wins and 52 nominations, Nelson has earned several prestigious awards such as a Kennedy Center Honor and the Library of Congress Gershwin Prize for Popular Song.

Dolly Parton released her debut album, "Hello, I'm Dolly," in 1967.

Dolly Parton released her debut album, "Hello, I
Dolly Parton in 1979.      Tsugufumi Matsumoto/AP

"Hello, I'm Dolly" reached No. 11 on the US country charts. The song "Dumb Blonde" reached No. 24, and "Something Fishy" rose to 17 on the country singles charts.

She has since won eight Grammy awards, as well as a Grammy Lifetime Achievement Award.

She has since won eight Grammy awards, as well as a Grammy Lifetime Achievement Award.
Dolly Parton today.      David Crotty / Contributor / Getty Images

Parton plans to release a new Christmas album in 2020.

Reba McEntire's self-titled debut album was released in 1977.

Reba McEntire
Reba McEntire in 1984.      Mark Humphrey/AP

It took until 1982 to achieve her first No. 1 hit, "Can't Even Get the Blues."

McEntire's 33rd album came out in 2019.

McEntire
Reba McEntire today.      Michael Loccisano/Getty Images

McEntire won best female vocalist at the Country Music Awards for four years in a row between 1984 and 1987. She also branched out into acting with the sitcom "Reba" that aired from 2001 to 2007.

George Strait released his first single "Unwound" in 1981 and it reached No. 6 on the Billboard charts.

George Strait released his first single "Unwound" in 1981 and it reached No. 6 on the Billboard charts.
George Strait in 1985.      Paul Natkin/Getty Images

He became known for hits like "All My Ex's Live In Texas," "I Cross My Heart," and "I Saw God Today."

In total, Strait has released 28 albums in 33 years.

In total, Strait has released 28 albums in 33 years.
George Strait in 2019.      Chris Pizzello/Invision/AP

Strait is the only artist who has won CMA's Entertainer of the Year award in three different decades and has had 44 songs reach No. 1 on the Billboard country charts.

Garth Brooks got his start in 1989 with a self-titled album that gave him his first No. 1 hit.

Garth Brooks got his start in 1989 with a self-titled album that gave him his first No. 1 hit.
Garth Brooks in 1989.      Beth Gwinn/Getty Images

"If Tomorrow Never Comes" was his first No. 1 hit, and three of the album's singles broke into the top 10.

Brooks earned the title of best-selling solo artist in US history in 2015, beating out Elvis Presley and only trailing The Beatles.

Brooks earned the title of best-selling solo artist in US history in 2015, beating out Elvis Presley and only trailing The Beatles.
Garth Brooks today.      Ethan Miller/Getty Images

Brooks has sold over 156 million albums over the course of his career.

Alan Jackson's first No. 1 single was "I'd Love You All Over Again" from his 1990 debut album, "Here in the Real World."

Alan Jackson
Alan Jackson in 1991.      Tim Mosenfelder/ImageDirect/Getty Images

Jackson wrote the song for his wife for their 10th wedding anniversary. The success of the single helped his first album sell 2 million copies.

Jackson has since won CMA's Entertainer of the Year award three times and was inducted into the Country Music Hall of Fame in 2017.

Jackson has since won CMA
Alan Jackson in 2017.      Terry Wyatt/Getty Images

Among his No. 1 hits are country classics like "It's Five O'Clock Somewhere," "It Must Be Love," and "Don't Rock the Jukebox."

Tim McGraw's first album came out in 1993, but it was his second album that propelled him to stardom.

Tim McGraw
Tim McGraw in 1994.      Paul Natkin/WireImage/Getty Images

McGraw's second album, "Not a Moment Too Soon," gave him his first No. 1 hit with "Don't Take the Girl" in 1994.

He has won three Grammy awards and had 26 Billboard No. 1 hits.

He has won three Grammy awards and had 26 Billboard No. 1 hits.
Tim McGraw today.      Frederick Breedon IV/Getty Images

"Wild One," Faith Hill's first single in 1994, spent four weeks at No. 1.

"Wild One," Faith Hill
Faith Hill.      The LIFE Picture Collection via Getty Images

Her first album went triple platinum and earned her the title of Top New Female Vocalist at the 1994 ACM Awards.

She has won five Grammys and been nominated 17 times.

She has won five Grammys and been nominated 17 times.
Faith Hill today.      Photo by Michael Loccisano/Getty Images

Hill and her husband, Tim McGraw, are a major country power couple. They've been married since 1996 and have toured and collaborated together throughout their respective careers.

Kenny Chesney signed his first record deal in 1993.

Kenny Chesney signed his first record deal in 1993.
Kenny Chesney in 1999.      Mark Humphrey/AP

He released "In My Wildest Dreams" in 1994, but the record label's country division folded and the album wasn't a success. A year later, he signed with a different label and put out "All I Need to Know," which featured two singles that broke into the Top 10 singles charts.

Chesney has had 11 No. 1 hits and 16 top 10 hits throughout his career, according to Billboard.

Chesney has had 11 No. 1 hits and 16 top 10 hits throughout his career, according to Billboard.
Kenny Chesney in 2019.      Leigh Vogel / Stringer/Getty Images

His latest album "Here and Now" was his 17th to top Billboard's Top Country Albums chart. Garth Brooks and Willie Nelson have also achieved 17 chart-topping albums, but George Strait holds the current record with 27.

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