Whatever Happened To Gretchen Wilson?

Gretchen Wilson was undoubtedly one of the biggest Nashville stars of the 2000s. She scored three consecutive No. 1 albums on the Hot Country Albums, with "All Jacked Up" even reaching pole position on the Billboard 200. And the Illinois native received 10 Grammy Award nominations, picking up Best Female Country Vocal Performance for "Redneck Woman." 

Speaking to the Los Angeles Times about the hit song, Wilson affirmed that she was simply speaking her own truth in the lyrics — one that many other women could likely relate to but weren't exactly hearing in other country songs at that time. "A redneck woman is hard-working, she's raising a family and holding down a job at the same time and is proud of who she is, no matter what," she said. That sentiment can certainly be applied to the highs and lows of the musician and proud mom's entire career. 

At the end of the decade, she left Sony's Columbia Nashville to form her own Redneck Records label, and Wilson's success began to dwindle. She hasn't come close to hitting the top spot on any kind of chart and the Grammys panel hasn't recognized her since 2011. So, what exactly happened to the one-time country music favorite? Well, Wilson has certainly had her fair share of drama, but she's also still out there performing the country music she made her name with — proudly, no matter what. Here's a look at her recent life story.

As tabloids love to eagerly remind readers, there seems to be something about airports that brings out the worst behavior in celebrities. And in August 2018, Gretchen Wilson added her name to this hall of shame when she was charged with a breach of peace misdemeanor at Connecticut's Bradley International Airport. A source had told TMZ that the "Redneck Woman" singer had gotten into a fight with another passenger aboard an American Airlines flight from Washington D.C. After landing, the star was arrested and then charged by state police after acting belligerently toward them.

Wilson addressed the alleged incident a week later, informing her Facebook followers that she couldn't go into details due to legal reasons. However, just a few days later, she did claim to Taste of Country that the tabloid version of her troubles was far from the truth. "People who know me know that I just wanna get it straight," she said. "I'm reading all of these headlines ... like, 'Oh gosh, it's so wrong, it's all so wrong!'" 

In September 2018, the charges against Wilson were eventually dropped. In order to settle the charge, Wilson agreed to donate $500 to a charity.

Just two years after the Connecticut airport incident, Gretchen Wilson once again found herself in the headlines after she was accused of creating a disturbance. On this occasion, the Hotel Encanto in Las Cruces, New Mexico was the scene of all the drama. But once again, the country star claimed she was entirely innocent.

According to the 911 call made by a hotel staff member, Wilson and her fiance had been asked to quieten down several times after numerous complaints from fellow guests. "Her words [were], 'I paid for the room — I could care less what people think,'" the employee in question claimed, per Page Six. The staff member added, "Her level of talking is like our yelling." However, bodycam police footage obtained by the Associated Press threw some doubt on claims on either side of the argument. 

According to the outlet, the video shows cops talking with a calm and composed Wilson in the hallway before they enter her room. Despite having told them, "We don't even have a TV on. We were very quiet," the room is totally dark save for the light from the television. After cops deduced that no noise crime had been committed, Wilson was told that the hotel manager decided she and her fiance could stay. However, she assured them she was leaving immediately for another establishment, stating, "We have been treated like s*** since we've been here." Wilson later implored her Twitter followers to boycott the offending hotel.

Growing up, Gretchen Wilson lived in the small town of Pocahontas, Illinois, which had a population of approximately 800 people at that time. The musician no doubt experienced quite the culture shock when she was thrust into the Grammy Award-winning, chart-topping limelight. In a 2017 interview with The Boot, the singer revealed that she struggled to adapt. "I spent my whole life looking for that moment, but as prepared as I thought I was, I wasn't. It happened so fast. I had a major label deal at the time, and I think that they thought that I was the next Shania Twain," she explained. "There was one trip that, I think, we crossed the International Date Line three times in a week and a half. I didn't know what day it was."

To make things even more challenging, Wilson was also busy juggling her music career with motherhood having given birth to daughter Gracie in 2000. The country music favorite often took her offspring out on tour with her, something she now realizes was a recipe for chaos, stating, "Can you imagine flying to Australia and worrying where the Ovaltine and diapers and stuff like that are? It was kind of nutty in the beginning."

From her 2004 debut "Here for the Party" up to 2013's "Right on Time," Gretchen Wilson spent a lot of time on tour. And having spent so many years on the live circuit, the country star perhaps inevitably ended up experiencing one of the most recurring pop star problems: total and utter burnout.

Speaking to The Boot in 2017, the "When I Think About Cheatin'" singer admitted that she needed some lengthy "me time" to recuperate from life on the road. "It wasn't just summertime touring — it was all year, a lot of the year, every year, for 12 years," she said. "I got wore out. I feel like everything got wore out, not just vocally, but I, just physically, got wore out, and I needed a little time off." Wilson was aware of how lucky she was to be in the position to press pause on her career, adding, "Not too many people get to go, 'I'm going to stay home with my kid for two years' ... so I feel very fortunate that I got to do that. But that time gave me the [desire] to get creative, too ... It gave me time to think." That same year, Wilson announced her return to the stage to promote her seventh studio effort "Ready to Get Rowdy."

You might not expect country music golden girl Faith Hill to have been a major source of inspiration for proud redneck Gretchen Wilson. But in a 2020 interview with Taste of Country, the latter revealed that she owes much of her career to the former.

Wilson recalled how she and John Rich, the Lonestar bassist who co-produced her 2004 debut album "Here for the Party," were once watching music television when the promo for Hill's "Breathe" popped up. The singer said, "She's gorgeous. She looks like a supermodel. She's rolling around in satin sheets ... I looked at John and said, 'This is probably never gonna happen for me because I'll never look like that, and I'll never be that. That is just not the kind of woman I am.'"

Rich encouraged Wilson to embrace the kind of woman she is, and the result was "Redneck Woman," the track which not only topped the US Hot Country Songs chart but also won the Grammy Award for Best Female Country Vocal Performance. The star added, "For a long time, I feel like in country music, women had gotten so slick and soft and pretty. So being authentic and being real, that is what got me to this dance."

Kid Rock is another one-time country music favorite whose commercial fortunes now appear to be in decline. But that didn't stop Gretchen Wilson from roping him in for her 2017 comeback album "Ready to Get Rowdy." Indeed, the pair, who have been friends since the mid-'00s, joined forces on the track "Bad Feeling."

While promoting the record, Wilson told Rare Country (via American Songwriter) that she and Rock first forged a connection after meeting at producer John Rich's 30th birthday bash. "We started talking and, ever since then, we get together whenever we can, whether that's to drink some beers or make some music." The Grammy Award winner also revealed that "Bad Feeling" was inspired by one particular get-together in which the American Badass was clearly going through a rough time.

"He was sort of a mess over everything, and I just left with this song sort of in my head," Wilson remarked. "I got together with a couple of amazing songwriters and got to writing. We trade favors. It was [Rock's] turn, so I asked him to sing on it with me, and I was really impressed with his vocals." Luckily, Rock's state of mind had improved by the time he headed into the studio with his long-time pal.

Born at the turn of the century, Gretchen Wilson's daughter Grace Penner is now a film production manager who recently graduated from Belmont University. And her country singer mum couldn't be prouder, as she told John Rich, her long-time producer and host of "The Pursuit!" in 2020. "My daughter is the first person in my family's history to go to college, and she wouldn't be there if I hadn't decided that I can do both things [being a mom and a successful musician]," she said. "I can imagine life without this career. Couldn't imagine it without her."

Wilson admitted that she feared her musical dream would shatter once she fell pregnant with Grace. "I was in the middle of recording and in big-time studios in Nashville, Tennessee, with big-time people. And my career was taking off and it was amazing. And then all the sudden boom ... I thought it was all going to come to an end." However, once Rich, who produced Wilson's 2004 debut album "Here for the Party," reminded her that Loretta Lynn had multiple children, the star recognized she could be both a mother and Grammy Award-winning, chart-topping star.

Gretchen Wilson may have been quiet on the musical front as of late. But she still has at least one foot in Nashville waters as the mentor of an emerging country singer. The singer signed Jessie G (not to be confused with "Price Tag" hitmaker Jessie J) to her Redneck Records label in 2018 and has been very much a hands-on boss since.

Speaking to Taste of Country, Wilson remarked that she was immensely proud of her protégé, an Oregon native who previously worked as a commercial fisher. "There's not a lot of women that I come across that are as tough as she is," she said. "There's a lot of girls that sing pretty. There's a lot of girls that look great and could probably go out there and probably have a career for a minute. But there's not a lot of girls that have the strength to endure what this is really all about."

Wilson acknowledged that she can be a bit overbearing when it comes to the ins and outs of guiding Jessie's career. But the latter insisted that she has nothing but love for the woman who plucked her from obscurity, saying, "She's got one of the biggest hearts ever and that makes her a great boss."

After several years away from the live circuit, Gretchen Wilson decided to return to the road in 2018 for a tour alongside Redneck Records signing Jessie G. "The Workin' Women Tour" was a little less exhausting than her previous itineraries. Only a handful of headlining shows were announced alongside performances at intriguing-sounding events such as Obetz Zucchinifest and the Tennessee Soybean Festival.

In an interview with The Boot, Wilson explained that she was taking things much easier this time around in order to avoid the burnout of her earlier days. The "Work Hard, Play Harder" singer also admitted that after such a long time away from the stage, she was a little apprehensive about playing in front of a crowd again.

However, Wilson acknowledged that the lure of performing had ultimately been too hard to resist. "I've missed that a lot, more than I think I know," she said. "I've missed being onstage and just feeling the excitement from the crowd and hearing them sing my words back to me. It's the greatest high on Earth. It's a lot of emotions; it's a lot of different feelings all balled into one."

Gretchen Wilson got the Christmas present of her dreams in 2018 when she was invited to work with one of her all-time musical icons — Bill Anderson. While she didn't actually get to sing alongside the legendary singer-songwriter, she was instead asked to put on a fast-food uniform for the music video for "Waffle House Christmas," the festive single from his 72nd studio album, "Anderson" (yes, 72nd!).

Wilson joined several other country singers in the promo including Tanya Tucker, Jeannie Seely, and her close friend Kid Rock. And in a press release for the clip, the chart-topper revealed she couldn't have been more excited at the prospect. "I am so grateful that I was asked to be involved in something like this," she said. "I've been such a fan of Bill Anderson for so long. And I get to hang out with my heroes!"

But as she explained, this wasn't the first time that Wilson had donned such an outfit. "I also had a Waffle House uniform in my closet from a television special we did several years ago, so it's been a lot of fun being part of this music video." It also wasn't the first time that she'd embraced the holiday season in her career. In 2013, she released the Yuletide album, "Christmas in My Heart."

Having scored a U.S. Country number one with "Redneck Woman," Gretchen Wilson was undoubtedly a no-brainer when it came to selecting ambassadors for Redneck Riviera Whiskey in 2018. The Grammy Award winner joined fellow country stars Colt Ford and Granger Smith to promote the brand owned by John Rich, the producer of her 2004 debut album "Here for the Party." In a press release about the partnership published by Business Wire, Wilson said, "When John and I wrote 'Redneck Woman' 15 years ago, little did we know there would be a Redneck Riviera Whiskey someday. While that [song] changed my life, here's to hoping this whiskey will change your attitude."

Let's just hope that Rich didn't read the interview Wilson gave to High Octane a year later. When asked about her personal evolution, the Nashville favorite answered, "We all get older; my drink of choice has graduated just like my age has. I'm more of a red wine sipper now. I still get on the Jack Daniels every once in a while, but I also get up every morning and get on the John Deere zero turn and mow the yard and work outside."

Gretchen Wilson has always been something of a George Jones fangirl. In a 2004 Billboard article, the singer revealed that after opening for the country legend, she would stand at the side of the stage just to get a glimpse of him and that she'd sneakily touch his guitar, too. Wilson has continued to pay her respects following his death in 2013. Six years later, she joined her Redneck Records protégé Jessie G for a performance of "Stacy" at the George Jones Museum. 

In 2023, she then joined the likes of Brad Paisley, Trace Adkins, and Dierks Bentley at "Still Playin' Possum: Music and Memories of George Jones", a tribute show held at Huntsville's Von Braun Center. Wilson performed "I Always Get Lucky with You" at the event, a ballad originally recorded by Merle Haggard in 1981 but released as a single two years later by Jones. Alabama.com was full of praise for the Grammy Award winner's interpretation, writing that she "brought grit" to what was Jones' final U.S. Country chart No. 1 single. 

During the '00s, Gretchen Wilson amassed five nominations at the Country Music Association Awards, winning Female Vocalist of the Year in 2005. But the Tennessee native was snubbed by the event throughout the following decade. That is, until she was invited back to its stage in 2019 for a celebration of women's contributions to country music. Wilson joined an all-star medley of some of the greatest country songs ever performed by women alongside such artists as Terri Clark, Martina McBride, and the show's co-host, the ever-entertaining Dolly Parton. As part of that performance, Wilson was able to belt out her 2004 chart-topping debut single, "Redneck Woman." But the highlight of the singer's night may well have been her interaction with one of the night's co-hosts.

A publicist for Wilson told Country Now that during a rehearsal for the ceremony, the "Come to Bed" hitmaker complimented Parton on her black rhinestone pants, adding that she'd like to find a similar pair herself. Instead of simply offering directions to the nearest boutique, the country legend generously offered her own pair. Wilson gleefully accepted and wore the pants on the night itself.

In the latter part of the 2010s, Gretchen Wilson was in the midst of a flurry of activity that she hoped would result in a career revival. In the spring of 2020, however, the COVID-19 pandemic slammed the brakes on those plans; not only did the pandemic shut down all live concerts, but the virus itself did a number on the singer. 

"So, I got COVID," she revealed in a subsequent interview with Fox News. "I was one of the very first to get it, and it was a heck of a round." According to Wilson, the symptoms she experienced were severe, ranging from hypertension to asthma and shortness of breath, which remained even after the virus had run its course. In fact, it took her many, many months to source the proper medical attention and be prescribed the appropriate medication to lower her blood pressure. "I mean, it was pretty severe. It was bad enough that I couldn't even do light housework without the blood pressure going up to scary levels," she recalled.

Years later, Wilson was still experiencing the effects of long-haul COVID. "I've got medications I'll have to take for the rest of my life — high blood pressure, asthma — these are all things I didn't have right before COVID," she told Billboard.

The lingering impact of the coronavirus wasn't the only health issue that Wilson experienced during that time. As she revealed in an interview with Parade, she'd also suffered a serious accident. "I also kind of fell and broke both of my leg bones and shattered my ankle," she said, noting that her leg was in a cast for eight months, during which she required a wheelchair to get around. She also explained why that hadn't been public knowledge earlier. "And I don't get on social media and go, 'Wah!' So I just didn't tell anybody," she added. 

Speaking with Billboard, she shared details of the accident that put her out of commission for the better part of a year. "I also was dancing with a 6-year-old boy at a wedding, spinning, spinning, spinning, then I lost myself and I shattered my ankle and my leg," she said.

That particular trait, she told Fox News, is nothing new and is simply part of who she is. "I don't get on my phone and go, 'Oh, woe is me and look at me and I am so sad, boohoo.' It's just not my personality," she said. With nothing to promote and in need of rest and recuperation, she decided to retreat from the spotlight until she felt she was healthy enough to return. "Like I said, it took a long time, but I finally got myself into a place where I was like, 'Okay, I feel like I'm back,'" Wilson explained.

After her self-imposed exile to recuperate from health concerns, in June 2024, Gretchen Wilson returned to the forefront to release a new single, "Little Miss Runner Up." Her first new music since 2018, the track was a sequel to one of her earlier hits, "Homewrecker." Written by the songwriting team of Rivers Rutherford and George Teren — who also composed the original — the song found Wilson returning to familiar territory. "'Little Miss Runner Up' follows the same girl we all know and love to roll our eyes at," she said in a statement to American Songwriter. "Can't wait to see how this song looks in a country music video."

She didn't have to wait long. The music video arrived just a few months later, making its debut in October of that year on the CMT channel. It was also shown repeatedly on Paramount's video billboard in NYC's Times Square. "CMT has been in my corner for over 20 years," said Wilson in a statement, via Country Music News Blog. "I can't thank them enough for their support and for all of this incredible exposure for 'Little Miss Runner Up.'"

The single placed her back in the spotlight, leading her to announce plans for a 20th-anniversary tour (co-headlining with country duo Big & Rich), and putting out more music the following year. "It's been a very successful year," she said of 2024 in an interview with Taste of Country. "I'm having a blast, I feel healthy, I feel good, I feel strong."

In the summer of 2024, Gretchen Wilson placed her home on the market. Situated in Lebanon, Tennessee — a suburb of Nashville — Wilson's asking price was $625,000, just under $100,000 more than she'd paid for it back in 2021. While the home is certainly comfortable, it's not nearly as lavish as one might expect, with three bedrooms and two bathrooms in 2,225 square feet. 

Wilson wound up selling the place just a few months after listing it, with the buyer reportedly paying $630,000 — $5,000 above her asking price. In a subsequent interview with Taste of Country, Wilson explained that the deal only went through because she agreed to the buyer's demands. "I sold a piece of property, and they wanted all of it," she said, explaining that the buyer wanted not just the house itself but a lot of the possessions within it. "They wanted my mowers, they wanted my pool table, they wanted my pool sticks," she explained. "I had to leave a lot of my stuff in that house when I walked away."

By September 2024, the U.S. presidential election was heating up. America was divided, and sides were being chosen after incumbent Joe Biden dropped out of the race after a disastrous performance during his debate with opponent Donald Trump, with former Vice President Kamala Harris becoming the Democratic nominee.

While many entertainers choose to avoid discussing politics for fear of alienating fans, Gretchen Wilson is not among that group. In fact, she declared her intention to vote for Trump and his Make America Great Again platform when she appeared at one of his campaign rallies, where she also performed. When addressing the crowd, the former Democrat revealed why she'd shifted her support to Trump's "Make America Great Again" movement. "Now, back in the day, my family were all Kennedy Democrats, but that's when the Democrats were on the side of the people," she said. "Once I started paying attention to what was really going on, I realized the Democratic party left us."

One part of Trump's platform that clearly connected with Wilson was his stance on tightening up America's borders and deporting undocumented immigrants. "I sometimes feel like in country music, we're a little like the border — a little too wide open. Everybody's like, 'Come on in!'" she told Taste of Country when posed a question about pop acts dipping their toes into country music.

In May 2025, Gretchen Wilson made an unexpected appearance on American television screens. It all took place in the season finale of Fox's bonkers singing competition "The Masked Singer," in which a panel of celebrities must guess the identity of a celebrity performer whose identity is concealed beneath an elaborate costume. In the finale, a costumed performer dubbed Pearl was declared the winner and revealed as Wilson when she removed her mask. 

For Wilson, appearing on the show came at a tenuous time in her life, right after she'd spent a few years off the radar to recover from various health ailments. "This just happened to come at a point in my life where I had a lot to prove to myself," Wilson told TooFab. "I had been kind of out of the spotlight for about two-and-a-half years, and I hadn't told anyone why."

Interviewed by People, Wilson admitted that returning to the stage — even hidden by a mask — was invigorating, both personally and for her music career. "I feel like it's sort of a comeback moment," she declared. "I'm ready to take on anything." Looking ahead to what may be awaiting her in the future, she was ready to enjoy the ride. "I have no idea what life's going to bring, what challenges, what rewards, what craziness might come," she added. "Whether it's familiar or unfamiliar, let's just see how it goes at this moment."

At the same time that Gretchen Wilson was covertly competing on "The Masked Singer," she was in talks to join another high-profile network television show. Previously, CBS announced country music powerhouse Keith Urban would star in "The Road," produced by his fellow country star Blake Shelton and "Yellowstone" creator Taylor Sheridan. Reportedly, up-and-coming artists would open for the singer in various parts of the country in the name of discovering new talent.

The network subsequently announced that Wilson had been tapped as well, in the capacity of "tour manager," serving as a sort of coach to the aspiring singers. "Stepping into the role of 'tour manager' for 'The Road' has allowed me to take everything I've learned over all of my years of touring and pour it right back into these emerging musicians," she said in a press release. Helping them sharpen their talents to capture the attention of these crowds across America and guiding them through the real and raw grind of life on the road, has been a highlight of my career."

In addition, Wilson will also be performing on the show. Planned to debut at some point in 2025, as of May 2025, a premiere date had yet to be set for "The Road."

Gretchen Wilson burst upon the country music scene in 2004 with her debut album, "Here for the Party," and breakout single "Redneck Woman." More than two decades later, she announced a plan for that album that could have been plucked from the playbook of Taylor Swift, whose power plays have reshaped the music business. 

Citing Swift's "Taylor's Version" re-recordings of her old albums, Wilson revealed she planned to do the same for "Here for the Party" — albeit with some surprising twists. "I am gonna do my version, sort of the way Taylor did, but on my label [Redneck Records]," Wilson explained in an interview with Billboard. "But instead of just recreating it the same way, I am going to have a guest vocalist on each song." According to Wilson, she'd already lined a few stars confirmed but wanted to wait until after "The Masked Singer" to reach out to more. "I've got a few absolute yes's so far, but I was waiting for this [post-'Masked Singer'] moment so that when I make the rest of the calls they are quicker yes's."

Among those who will for sure be on the reimagined, rebooted album are Travis Tritt and country duo Chapel Hart, while some "huge names" are also in the running. "I want to make sure [they know] I'm not trying to reinvent myself with the album, I've got other things going on and this will be good for them," she said, explaining why she hopes big stars will participate.

While Gretchen Wilson was reaching out to big stars to join her on her re-recorded version of "Here for the Party" two decades later, she was also using her own fame to help bolster the careers of up-and-coming country artists. Wilson joined singer-songwriter Alli Walker on a 2025 single, "First Time Living." When Wilson first heard the track, the instant connection she felt with the material made it a no-brainer to participate. "And I just cried my eyes out all the way through listening to it because it sounded like my story and no one had really connected with it lyrically in that way before," she said in a statement, via Anti Music.

Wilson also teamed up with singer Ira Dean, providing harmonies on his 2025 single, "Everything." With the song written for his wife, Dean called in a favor from Wilson, an old pal. "I called my long, long, long-time friend Gretchen Wilson and asked her to sing on it, and she did an amazing job," Dean said, as reported by The Music Universe.

In conjunction with hitting the two-decade milestone of the release of "Here for the Party," Gretchen Wilson decided 2025 was the right time to return to the road. Her Still Here for the Party Tour — kicking off in early 2025 — followed her joint tour with Big & Rich, marking her first solo tour since 2019. "Seeing fans lose their minds at every tour stop and on the two performances at CMA Fest last year really gave me the spark I needed to get back out on the road," Wilson says in a press release (via Taste of Country). "My band and I have been rehearsing like crazy, and I can't wait to share this music with old fans and make some new ones."

In that release, Wilson promised fans that they'd be experiencing a career-spanning set featuring songs throughout her catalog, particularly from her first few albums. "I'm also digging deep in my catalog and playing songs from those early albums that I haven't played in a while," she said. "People ask me about songs like 'Pocahontas Proud,' 'Trucker Man,' and 'All Jacked Up,' so we're breaking those out, too."