Mark Wills was part of a fresh-faced crop of rising country artists that found their way in the late '90s. With the likes of Tim McGraw, Lonestar, and Faith Hill all carving out a new lane in which to work in —one that continued to blend pop sensibilities into country music — Wills too found a comfortable place to thrive in.
Much like Collin Raye, Wills' best music efforts were found on incredible ballads about love and heartbreak. Breakout songs like "Wish You Were Here," "Jacob's Ladder" and "Don't Laugh At Me" weren't only catchy, they were filled with powerful statements about life in general. Though he rarely wrote any of his best-known singles, Wills had an uncanny ability to pull the greatest meaning out of them with heartfelt vocal deliveries. They had a seriousness to them.
In some respects, Wills was a little before his time. Albums like Permanently and Loving Every Minute weren't the box office smash hits like some of his contemporaries, but they were strong efforts marked by their dynamic song structures that often took inspiration from outside country music while still maintaining a country influence.
In the mid and late 200s, Wills continued to mix up his music. At this point, for better or worse, he had been pigeonholed as only a love ballad and sad songs artist due to his most well-known singles. Albums like And the Crowd Goes Wild, Familiar Stranger, and Looking for America were able to help shake the stereotype since they found a looser and more rocking version of Wills.
With seven full-length albums and eight Top 10 singles under his belt, Wills' music career found the Georgia native delivering some of the most memorable songs of the late '90s and early '00s. Here are 15 of Wills' best songs.
15. "19 Somethin'"
In 2002, Wills released "19 Somethin'," the greatest crossover hit of his career. It rose to 23 on Billboard's Hot 100 and wound up sitting at number three on the U.S. Country Songs' Year-end list. It was a massive shift from Wills' typical slow love ballad stylings. Here, we saw him letting loose and cutting up on the catchy fast-paced rocker. It was filled with plenty of nostalgic references to the '70s and '80s—Stretch Armstrong, Evil Kinevil, 8-tracks and so on.
14. "She's In Love"
"She In Love" was the fourth single from Wills' strong Wish You Were Here sophomore efforts in 1999. Though it plays out much like a classic love ballad with strong harmony vocals and a warm sonic blend, we again we Wills coming up short in the love game. He notes that his former flame and current friend looks as though she's really fallen in love, but just wishes it'd have been with him instead.
13. "Back At One"
On Permanently, Wills would dip into the R&B world and cover Brian McKnight's breakout hit "Back At One." Much like McKnight's, Wills' version would have mass appeal on the country charts. Though it certainly had a country music edge to it, Wills would still deliver the love song with a soulful spin.
12. "Loving Every Minute"
Wills' fourth studio album, Loving Every Minute, was marked by its sharp pop sense and crisp country tones. Though it only produced two singles, the title track and the Jamie O'Neal duet "I'm Not Gonna Do Anything Without You," it was perhaps Wills' strongest and most mature sounding album of his career. "Loving Every Minute" was only get to 18 on the Billboard U.S. Country Charts, but it was one of Wills' most dynamic efforts to date.
11. "Never, Ever and Forever"
Back in 2000, Wills, Lee Ann Womack, and Rhett Akins starred in an animated musical of Tom Sawyer. Wills, who voiced Huck Finn, and Womack, who voiced Becky Thatcher, sing the lovely and mostly unknown duet "Never, Ever and Forever" for the animated film. As you'd expect, Wills and Womack's voices blend together elegantly on the light and airy love ballad.
10. "High Low And In Between"
Released in 1996, "High Low And In Between" was only the second single of Wills's career. Much like "Jacob's Ladder," the underrated "Ace of Hearts" and "Leavin' Comin' On," "High Low And In Between" played to Mark Wills' countrier characteristics. Like the mullet he was rocking (it was the '90s!), "High Low And In Between" is as free-flowing a moment you'll see in the Wills catalog.
9. "I'm Not Gonna Do Anything Without You"
As mentioned prior, Wills and O'Neal's "I'm Not Gonna Do Anything Without You" helped create Loving Every Minute's mature sonic palette. Wills and O'Neal have a natural chemistry that just pops out through the speakers for spectacular results. It's undeniably more of a step into the pop world, but there are still country roots with its warm pedal steel swells.
Wills' career is filled with plenty of "what if" moments. He'd cut "What Hurts The Most" a few years before Rascal Flatts as well as "Somebody" before Reba McEntire. Both would end up being number-one singles. Perhaps due to the lack of commercial success with the other singles on Loving Every Minute "Somebody" never got the chance by Wills. Still, it's as strong an effort as McEntire's.
7. "I Do (Cherish You)"
While most of Wills's career song him dipping into the R&B and pop world for influence, we'd see the opposite happen on "I Do (Cherish You)" when boy band 98 Degrees would also record the heartfelt love ballad. Written by Allen Shamblin and Dan Hill, Wills' delivers some of his best vocals on the power ballad.
6. "Almost Doesn't Count"
Like "Back At One" before it, "Almost Doesn't Count" sees Wills recording "Almost Doesn't Count," an early Brandy single written by Shelly Peiken and Guy Roche. Again, Wills would give the love song a country music spin while also maintaining a soulful touch and pop sense.
5. "Don't Laugh At Me"
Wills would find success again with an Allen Shamblin co-write with 1998's "Don't Laugh At Me." Written by Shamblin and Steve Seskin, "Don't Laugh At Me" would rise to number two on Billboard's U.S. Country Charts due to its memorable chorus and an anti-bullying message. "In God's eyes, we're all the same. Someday we'll all have perfect wings," sings Wills on the melancholic hit.
4. "When You Think Of Me"
Like "19 Something," "When You Think Of Me" was found on Wills' 2002 Greatest Hits album. It finds Wills at perhaps his most ambitious with its soaring chorus, emotionally charged delivery, and anthemic rise. It'd only sneak into the Top 30 on the country music charts but really should have resonated more.
3. "Places I've Never Been"
"Places I've Never Been" was the third infectious love song single of Wills's young career. "I travel the world in your arms and back again. I have no need to wander or go chasing those four winds," sings Wills on the catchy singalong. Coming in at the tail end of the Neo-Traditional boom of the '90s, "Places I've Never Been" (along with the rest of his debut album), is easily Wills most country efforts. Still, there's plenty of pop sense along with the pedal steel and warm fiddle.
2. "Jacob's Ladder"
In 1996, Wills burst onto the scene with "Jacob's Ladder," the first single from his self-titled debut album. It'd rise to six on the charts and was as promising a start by anyone out of the crop of late '90s country artists. In hindsight, early singles by Wills had more of a storytelling narrative aspect (another being our top pick, "Wish You Were Here"). He'd slowly shift to more hard-hitting love songs and heartbreakers, but here, we're given both—sentimental love and a driving story. As most of Wills's singles did, it highlighted his warm and strong vocals with plenty of space for both aspects to shine.
1. "Wish You Were Here"
"Wish You Were Here" was the first number-one single by Wills. Hit top the charts in Spring of 1999 falling in line with other strong Wish You Were Here singles and Wills staples "I Do (Cherish You), "Don't Laugh At Me" and "She's In Love." Wills' love songs never felt mailed in or cavalier in nature. He rarely, if ever, sang about fair-weather flings or one night stands. When you think of Wills, it's an everlasting and neverending kind of love. That's the kind found on the heartwrenching ballad "Wish You Were Here." Written by songwriting veterans Skip Ewing, Bill Anderson, and Debbie Moore, "Wish You Were Here" was right in Wills' wheelhouse.
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