How some of these failed to go #1 is downright baffling. Throughout country music’s illustrious history, there have been many names who are up there in the greatest of all time (GOAT) conversation. From Johnny Cash, Willie Nelson and Merle Haggard to Dolly Parton, George Strait and Hank Williams, there have been plenty of worthy artists in the conversation. As time goes on, it’s become more apparent that Alan Jackson should also be mentioned among these greats. With nearly 60 million records sold worldwide, 14 certified-platinum albums from the RIAA, 19 ACM Awards, 17 CMA Awards, two Grammy wins, a Kris Kristofferson Lifetime Achievement Award from the Nashville Songwriters Association International (NSAI), placement in the Country Music, Songwriters and NSAI Songwriters Hall of Fame, 50 Top 10 hits and 35 #1 hits (including 26 on Billboard), the Georgia native’s list of career accomplishments seem endless. Beyond timeless hits such as “Chattahoochee,” “Where Were You (When the World Stopped Turning),” “Gone Country,” “Don’t Rock the Jukebox” and countless more, Jackson has not only topped the charts at one of the highest rates in the genre’s history but also became the voice of multiple generations over his nearly five-decade career. With his final concert Last Call: One More For The Road – The Finale, taking place tomorrow night at Nissan Stadium in Nashville, featuring the likes of George Strait, Eric Church, Luke Combs, Riley Green, Cody Johnson, Miranda Lambert, Lainey Wilson, Jon Pardi, Carrie Underwood, Keith Urban, Lee Ann Womack and more, I thought it would be a perfect time to look at some of his biggest songs that shockingly never made their way to the top of the charts. “Midnight in Montgomery” Jackson’s haunting, fictional encounter with Hank Williams’ ghost has remained one of the best and most unique in the “Chattahoochee” singer’s discography. Though it’s often regarded as one of his best, it is not among his 26 #1 hits on Billboard’s Hot Country Songs chart. It would peak at #3 in July 1992 behind the likes of Billy Ray Cyrus’ now infamous “Achy Breaky Heart” and Wynonna’s cover of “I Saw the Light.” Additionally, it was the only single from his sophomore album, Don’t Rock the Jukebox, that failed to go #1. Peak Chart Position: #3 “Mercury Blues” “Mercury Blues,” which is a cover from the rural blues group, K. C. Douglas Trio, received a lot of love commercially upon its release in 1993. Despite being used in a Ford commercial and being performed on the sitcom Home Improvement, the track was blocked from going #1 by Tracy Lawrence’s “My Second Home” in December 1993. Peak Chart Position: #2 “Murder On Music Row” One would think that the first-ever collaboration between two of the most popular artists in country music history, George Strait and Alan Jackson, would be a guaranteed #1. However, that wasn’t the case with “Murder On Music Row.” Of course, this can be attributed to the track taking direct aim at the current state of the music industry at the time and Nashville at large. Despite “Murder On Music Row” scoring the pair two CMA Awards for Music Event of the Year in 2000 and Song of the Year in 2001, it only peaked at #38 in April 2000. Peak Chart Position: #38 “Here in the Real World” You can most likely attribute the chart position for “Here in the Real World” being just his second career single. Though it was blocked from going #1 by Dan Seals’ four-week run with “Love on Arrival.” All things considered, it’s still a great showing on your second single and first Top 5 hit. Peak Chart Position: #3 “Pop a Top” Originally recorded by Jim Ed Brown in May 1967, “Pop a Top” was a Top 5 hit upon its release. Despite Jackson’s version being a fan favorite til this day, frequently being used on the likes of TikTok, it actually didn’t receive as much love as you’d expect. Though it was released at the height of his popularity in 1999, it peaked at #6, which feels a bit low for this infectious track. Peak Chart Position: #6 Alan Jackson’s 35 #1 Hits 1. “Here In the Real World” 2. “Wanted” 3. “Chasin’ That Neon Rainbow” 4. “I’d Love You All Over Again” 5. “Don’t Rock the Jukebox” 6. “Someday” 7. “Dallas” 8. “Midnight In Montgomery” 9. “Love’s Got a Hold On You” 10. “She’s Got the Rhythm (And I Got the Blues)” 11. “Tonight I Climbed the Wall” 12. “Chattahoochee” 13. “(Who Says) You Can’t Have It All” 14. “Summertime Blues” 15. “Livin’ On Love”  16. “Gone Country” 17. “I Don’t Even Know Your Name” 18. “Tall, Tall Trees” 19. “I’ll Try” 20. “Home” 21. “Little Bitty” 22. “Who’s Cheatin’ Who” 23. “There Goes” 24. “Between the Devil and Me” 25. “Right On the Money” 26. “It Must Be Love”  27. “Where I Come From” 28. “Where Were You (When the World Stopped Turning)” 29. “Drive (For Daddy Gene)” 30. “It’s Five O’Clock Somewhere” (feat. Jimmy Buffett) 31. “Remember When” 32. “Small Town Southern Man” 33. “Good Time” 34. “Country Boy” 35. “As She’s Walking Away” (Zac Brown Band)The post 5 Alan Jackson Hits That Surprisingly Did NOT Go #1 first appeared on Whiskey Riff.