Wynonna Judd Is a True Music Icon! See Photos of the Country Singer From Then and Now

1985

Wynonna, along with mom Naomi, rose to fame in the ’80s as a twosome known professionally as The Judds. The duo released five studio albums together from 1984 and 1991, scoring 14 No. 1 hits on the Hot Country Songs Billboard chart.

Here they are ringing in 1985 performing — likely with their song “Mama He’s Crazy” — on Dick Clark’s New Year’s Rockin’ Eve on December 31, 1985.

July 1990

The reason for their musical split? Naomi was diagnosed with Hepatitis C in 1991, leaving Wynonna to embark on a successful solo career. Nothing could take away all the accolades they had won during their time singing together — including seven from the Academy of Country Music, nine from the Country Music Association, and five Grammys. That’s quite the career, right?

December 1993

Wynonna met her first husband, Arch Kelley III, in 1993 and they married on January 21, 1996. At the time, the couple was already parents to son Elijah, born by C-section on December 23, 1994. On their big day she was also pregnant with their second child, a daughter named Grace, who was born on June 21, 1996. Wynonna and Arch divorced in 1998.

January 1994

The Judds reunited in 1994 for the Super Bowl XXVIII halftime show, performing with fellow country stars Clint Black, Travis Tritt and Tanya Tucker. Here they are during that momentous night, proving just how big of a deal they were!

September 1998

Wynonna and Naomi aren’t the only famous Judds out there — there’s Ashley, too! Ashley is Naomi’s daughter with her husband Michael — meaning she is Wynonna’s half sister. The two have remained tight throughout the years.

The actress is best known for TV shows like Sisters, Missing and Berlin Station as well as films like Kiss the Girls, Double Jeopardy, Where the Heart Is, High Crimes, De-Lovely and the Divergent franchise.

Here are the three lovely ladies at the Vanity Fair Oscar party in 1998.

February 2004

Wynonna was married to her second husband, former bodyguard D.R. Roach, from 2003 until 2007.

March 2005

Wynonna’s daughter, Grace, posed with her in March 2005 backstage at the Broadway production of Little Women when Grace was just 8 years old. (Notice Younger star Sutton Foster there on the right?)

April 2006

Essentially a country music-only version of American Idol, Nashville Star ran for six seasons from 2003 until 2008. Wynonna (pictured here) joined the show to host season 4 alongside Cowboy Troy — joining the likes of LeAnn Rimes, Jewel, and Billy Ray Cyrus who also said yes to the gig. The show is credited for introducing us to big stars like Miranda Lambert and Kacey Musgraves.

January 2011

Here is Wynonna promoting her first novel, Restless Heart. It’s not the only thing she has written, though, as the songstress penned a memoir titled Coming Home to Myself a few years earlier in 2005. We love a book queen!

February 2013

Wynonna competed on season 16 of Dancing With the Stars — partnered with Tony Dovolani. While the pair was the first to be eliminated, they were actually the second couple to leave (all because of Dorothy Hamill‘s injury).

September 2013

Unlike Grace, Wynonna’s son, Elijah, has had a smoother life.

August 2014

Third time’s the charm! Wynonna’s current husband, Cactus Moser, married the stunning redhead on June 10, 2012. Soon after the happy day, though, Cactus was involved in a motorcycle accident in South Dakota that resulted in the musician’s left leg being amputated above the knee. We wish them a lifetime of happiness!

October 2015

The Judds reunited yet again in October 2015 for a Las Vegas residency at the Venetian. Titled The Judds: Girls Night Out, they — for nine shows, at least — turned up the heat on the Strip.

November 2017

As a solo artist, Wynonna has put out eight studio albums and snagged four No. 1 hits on the Hot Country Songs Billboard chart. Wynonna hasn’t won as many awards as she did while performing with her mom, but this talented lady is still one of the best in the business. There’s no disputing that!

September 2018

Wynonna appeared on the reality show Real Country — which featured Shania Twain — as a celebrity guest. The singing competition sought to find emerging solo artists, duos and groups who could be the next breakout act.

September 2023

The singer looked flawless at the 2023 People’s Choice Country Awards.

December 2023

Wynonna looked absolutely stunning on the red carpet ahead of hosting the Christmas at the Opry special on NBC. She took the stage multiple times throughout the night, tackling some holiday classics in an array of gorgeous outfits.