10 Best Male Country Singers of the 90s You’ll Love

Discover the Best Male Country Singers of the 90s!

In my opinion, the best male country singers of the 90s are: Alan Jackson, George Strait, Toby Keith, Garth Brooks, Billy Ray Cyrus, Tim McGraw, Clint Black, Aaron Tippin, Mark Chesnutt, and Brooks & Dunn.

But what about these artists made them so special decades ago?  Well, let’s dive into each singer to find out!

Best Male Country Singers of the 90s

Let’s begin by talking about what made Alan Jackson special.

Alan Jackson

Is Alan Jackson one of the best country male singers of the 90s?

A small-town country boy from south-Georgia, Alan Jackson is one of the best-selling country artists of all time. He is well-known for his neo-traditional country style and for penning many of his own works. Jackson has sold over 75 million records worldwide and has had a record number of country hits. 

Jackson’s career began in ’89 with his debut single, Blue Blooded Woman. After the debut, his career took off. He saw a great deal of success in the 1990s with songs like Tall, Tall Trees and Little Bitty. Jackson has continued to consistently release hits through the 2000s and 2010s. He is currently touring on his “Last Call” tour, but it’s been pointed out that it’s not Jackson’s “Final” tour. 

Favorite Song

There are not many voices like Alan Jackson’s, and his style of music is unforgettable. Over the years, he’s released a record number of hits. But Drive is one of the best he ever wrote. What many don’t realize is that Jackson actually wrote that for his father, “Daddy Gene.” It’s full of memories of his childhood. Drive brings back many memories for all of us, and it shows how memories shape the way that many of us handle our lives later.

George Strait

George Strait is a down-home, country boy, born and raised in Texas. Strait, affectionately known as the “King of Country,” is regarded as one of the most well-known and significant musicians in history. His success began with his first single, Unwound, in 1981. Strait thrived during the 1980s and 1990s. 

Over the years, Strait has sold over 120 million records worldwide. He also expanded his career beyond the stage to the big screen, appearing as himself as a guest star in a few high-profile films. Straits has received a number of honors and awards since 1985—almost too many to count. He continues to bless fans with his voice to this day, still touring.

Favorite Song

All through his career, Strait has had so many great hits. Treasures in the world of country music. It makes a decision like this extremely difficult. However, the best song that’s ever passed George Strait’s lips is I Cross My Heart. Since its release date, the song has played at countless cowboy and honky-tonk, country weddings. It’s a beautiful ballad promising to love their partner no matter what—until the end of time.

Toby Keith

Toby Keith is one of the top country male singers of the 90s.

American country music singer, songwriter, and actor Toby Keith released his first album in 1993. From there, he became incredibly popular and successful. Over the years, he’s released over 19 albums, including Christmas and compilation albums. Songs like Beer for My Horses and As Good as I Once Was topped charts for a considerable amount of time. 

Beyond his musical career, Keith was featured in several productions, including Beer for My Horses and Broken Bridges. Keith is known particularly for his witty humor and sarcastic lyrics. He’s received a number of awards and honors. Currently, Keith is struggling with his health and has canceled his concert tour dates, but he may possibly return after his recovery.

Favorite Song

The best Toby Keith song is easily Courtesy of the Red, White, and Blue. The song simply states that if someone threatens the U.S.A., they will truly regret it. It is about national pride and the power of unity among Americans in the face of danger. Keith has never been shy on his feelings towards terrorists and what he’d like to do to them. He’s a patriot with a platform, and he definitely uses it.

Garth Brooks

Oklahoma was the birthplace and upbringing of singer, songwriter, and all-around musician Garth Brooks. He started out by moving from club to club and bar to bar through Oklahoma. Brooks’ first album, Hungry Years, was released in 1989 and was a chart success. From then on, Brooks has had major success in country music and crossover genres.

During his successful career, Brooks has had a couple of world tours. He’s also released a holiday album to add to his successful album list. Brooks continues to tour and release albums, and will do so for quite some time. A fun fact about Brooks: he loves baseball. He made an attempt at professional baseball in the late 1990s. With his success, Brooks has been very charitable, founding a number of organizations, including the Teammates for Kids Foundation. 

Favorite Song

With an endless supply of amazing Garth Brooks songs, it’s difficult to decide which one is the best. However, If Tomorrow Never Comes will always stick out in my mind. The lyrics serve as a reminder to tell your loved ones how you feel when you can. Tomorrow is never promised, so love them with your whole heart and let them know you do.

Billy Ray Cryus

Every one knows that infamous mullet that Billy Ray Cyrus sported in the early years of his career. His career consisted of 16 studio albums and 53 singles. Cyrus’ hit single, Achy Breaky Heart, was the first single ever to reach triple platinum status in Australia.

Cyrus was popular for his music career, especially in the 1990s. But he spread his wings a bit into acting with a role on his daughter’s hit show, Hannah Montana. After that, he continued to take parts in various TV series and films. 

Favorite Song

We all know the popular song, Achy Breaky Heart, however that doesn’t make it my favorite. My favorite of Cyrus’ songs is actually one that he sings about his daughter. Ready, Set, Don’t Go is sung from the perspective of a parent whose child is leaving home for the first time. It’s heartbreak and encouragement. Hopeful and somber. Exactly how most parents feel when their children leave the nest.

Tim McGraw

There aren’t many people who don’t know who Tim McGraw is. Even if you aren’t a fan of country music, you’ve likely seen him in one of his many acting roles, recognized his wife (Faith Hill), or heard of him in some other way. He began his career in the early 1990s with his debut album, Tim McGraw. Though the album was unsuccessful, he continued on to release more successful works.

Through the 1990s, McGraw became increasingly popular. His subsequent works saw greater success than the ones before them. He became a sensation. McGraw has continued recording, but has expanded his fame into the film industry. He has been featured on a number of shows and movies. McGraw has received a number of awards through the years for both his acting and singing. He has used his success charitably and is also known in the political world.

Favorite Song

Tim McGraw’s 1997 release, It’s Your Love, is one of the most passionate songs that has ever existed. McGraw has a special voice that is showcased well with the lyrics and melody. The song has been played at many country weddings for its simplistic references to commitment and undying love. Only his duet with Faith Hill elevates it. Together, they make the song utterly breathtaking.

Clint Black

American country musician Clint Black signed with RCA Nashville in 1989. Shortly after, his debut album released four number one singles on the country charts. Black had over 30 singles on the country charts and continued to consistently put out top-charting music well into the 2000s. 

Black ventured into acting, but mainly stuck with his musical talents. Because of his incredible talents, Black has received numerous award nominations. He has a traditional style that many fans enjoy, but he also ventures into Western swing and honky-tonk. Not only is he a great singer, but an incredible musician as well.

Favorite Song

Clint Black has a distinctive voice that few others can match. Like The Rain is a song that does well to showcase that spectacular vocal range. He has a particular sound, a growl, when he sings certain words. The lyrics are passionate, and Black’s voice matches that passion quite well.

Aaron Tippin

Aaron Tippin made his debut in 1991 with You’ve Got to Stand for Something. During this time, due to the Gulf War, the song became popular as an anthem for the soldiers who were fighting. Tippin struggled a bit after, with his next two songs falling flat. However, he continued to be a popular country artist through the 1990s as he released more successful songs.

Tippin’s baritone voice is characterized by its heavy Southern twang. When asked why he likes country music, his response was, “Why not country music? I grew up with it. What I like about it is that it tells a story.” He has received honors and nominations for them. While he hasn’t released anything new in a while, he is still touring and performing to this day.

Favorite Song

Tippin has quite a few great songs, but none top There Ain’t Nothing Wrong With The Radio. He has an incredibly unique voice; the instrumentals complement his twang extremely well in this particular song. You can tell he’s really feeling the music and the song when you hear him sing.

Mark Chesnutt

Mark Chesnutt had his greatest success in country music between 1990 and 1999. He is known for his neo-traditional and honky-tonk influences. Chesnutt has been compared to George Jones on more than one occasion. He grew up listening to the classics as a singer and songwriter from Beaumont, Texas.

While Chesnutt wrote and sang mostly his own songs, he also covered singles from quite a few other artists. He made Hank Williams Jr. and Conway Twitty proud on more than one occasion. His latest album in 2018 was a tribute to all of Chesnutt’s heroes, including Tammy Wynette, George Jones, Conway Twitty, and many more. 

Favorite Song

Mark Chesnutt has always had a special style. The steel guitar and his voice together—well, there’s just not much like it. Bubba Shot the Jukebox is an unforgettable, upbeat song with a little bit of humor and a lot of old country style. 

Brooks & Dunn

Brooks & Dunn are the male duet of the century. There really is no comparison to them. Formed in 1990, the duo took the country music industry by storm. Before they decided to come together to make this historic duet, they were both rising solo artists. They were popular for their mainstream country and honky-tonk influences. Most everyone who listened in the 1990s knew their songs when they came across the radio.

After years together, they performed their final concert in 2009. They continued to record as solo artists, and both have had successful works since. In 2015, they reunited for several concerts with Reba McEntire. Then, in 2019, they were inducted as a duo into the Country Music Hall of Fame.

Favorite Song

Red Dirt Road, Neon Moon, and Boot Scoot and Boogie are all well-known songs from Brooks & Dunn. However, my favorite is the extremely emotional, heartfelt song, Believe. The emotion in the lyrics and melody is incredibly strong. It’s just a reminder to never forget your past and always be grateful for who and what you have. 


The 1990s produced some of the best country music artists. From the new emerging artists to the old classic men, the best male country singers of the 90s are sure to never be forgotten. Listening to them brings back fond memories of childhood and stresses how much country music has changed since then.  

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