The 1983 CMA Single of the Year, besting efforts by fellow traditionalists Ricky Skaggs, George Jones, and Willie Nelson and Merle Haggard, “Swingin’” is a veritable feast for the senses, setting its cozy rural scene with young Charlotte Johnson’s brother eating chocolate pie on the sofa as her mama cooks up fried chicken in the kitchen. But it’s Charlotte and the song’s narrator who savor simpler delights as they cuddle together on the front porch swing, swaying back and forth to one of the most deliciously inviting country tunes of all time. —S.B.

Anderson didn’t write this track from his 1980 self-titled debut, but his vocal performance makes a song about a paranoid (or very astute) partner’s suspicions feel like a smooth country classic. In the glossy, Urban Cowboy Eighties, the Kent Robbins-written “She Just Started Liking Cheatin’ Songs” packs plenty of fiddle and honky-tonk spirit, but the slight doo-wop groove proves that Anderson was an artist with his own innovative spin on what the genre can do, and where it was going. It reached No. 13 on the Billboard Hot Country chart, and got a second boost in the late Nineties when Alan Jackson tackled it for his Under the Influence covers record. —M.M.

Opening with a lovely piano and fiddle part that portends its theme of loss and regret, this 1992 single went Number 2 on the Billboard Country chart with a subtle, forlorn environmentalist message. Anderson sings about the way economic progress leads to the degradation of natural beauty – the way we “dig for silver and for gold/And leave the empty holes.” He then homes in on the drainage of the Florida Everglades and the way that project impacted the Seminole tribes of the region. In the video, Seminole tribe members perform alongside Anderson. Despite its tone of indictment, the song’s catchy wistful melody can double as a nostalgic evocation of home for residents of the Sunshine State, so it’s no surprise that “Seminole Wind” is played by the Florida State marching band at Seminoles home games. –J.D.

When Anderson decamped to Dan Auerbach’s Easy Eye Studio in Nashville to make Years, he didn’t know it was going to be his last record. But, as he told Rolling Stone, after numerous health struggles, he sure was going to sing like it was. “If I’m gonna make one,” Anderson said, “I’m gonna make it like it might be the last one I’ll do.’” The title track, written by Anderson and producer Auerbach alongside Pat McLaughlin and David Ferguson, became a late-career standard frequently covered by Sierra Ferrell, including a version on a 2022 tribute LP. It’s a song that could be too melancholy or too toxic-positive in less adept hands: instead, it copes with the passage of time with a resigned sense of peace. The years pass too quickly, but it’s what we leave behind that matters. —M.M.

When Anderson released what would become one of his most well-known tunes — and a signature of early Nineties country music at large — he was a 37-year-old country singer wondering if his career was all but over. He kept switching labels and was playing off-the-radar- bars around the country. The perfect character sketch (a tale of a wine-sipping barfly with more regrets than she can count) changed everything for Anderson when it went Number One: “We’re in country music,” Anderson told a newspaper in 1992, “where a hit is the cure of all problems.” —J.B.

A wonderful deep cut tucked into the latter half of Anderson’s 1997 album Takin’ the Country Back, this is his ebullient entrant into the canon of “jump” songs, and it deserves to be mentioned right alongside Van Halen and the Pointer Sisters’ more famous ones. It’s a radiantly catchy tune about a poor, happily threadbare family who blows all their money on a backyard trampoline, even though they probably should’ve used it to get a new dryer. Their tramp becomes a metaphor for togetherness and fun for fun’s sake. “Daddy says life is such a crazy mess/He gotta jump on your chances for some happiness,” Anderson sings, and the song has the perfect amount of bounce to make you want to hop right in there with them. —J.D.

Inspired by a girl who “could party and rock harder than anyone I’d known,” John Scott Sherrill wrote this song while separating from his wife. The first country chart-topper for both singer John Anderson and Sherrill, “Wild and Blue” is a hauntingly beautiful account of a cheating woman, told from the POV of her cuckolded man. Anderson’s syrupy drawl and mournful wail is intensified by sister Donna’s Hill Country harmonizing. Lloyd Green’s pedal steel and twin fiddles paint a long, bleak evening of waiting for honey to come home, but in the end, the singer’s resigned forgiveness is hardly cause for celebration. Big-voiced Sally Timms gave Anderson’s 1982 hit a straight, strong reading when British country punks the Mekons covered it on 1991’s Curse of the Mekons. —R.G.

Anderson sells this tale of heartbreak and abandonment like no one else: Listen to how he alternates between  unabashedly enamored and wallowing in desolate dejection as he sings about a woman who shatters their former lovers’ heart when they get up and leave. Anderson’s unmatched ability to emotionally switch from one to the other — and to sell each emotion convincingly — is the entire song. The single came out in 1984, hitting Number Three on the Country Charts, and would end up being Anderson’s last Top Five hit of the Eighties until he reclaimed his spot at the top of charts, seven years later, with “Straight Tequila Night.” —J.B.

Three years after Tina Turner’s Foreign Affair LP turned this Tony Joe White-penned blues-rocker into a global smash, Anderson hit closer to home with a sultry country version for his 1992 comeback album, Seminole Wind. Problematic language about breaking down her defenses aside, there’s a backwoods charm to Anderson’s smooth delivery that suggests less carnal desire and more a consensual backseat romp to recapture misspent youth. —S.B.

Anderson told Rolling Stone that his rendition of Billy Joe Shaver’s I-am-what-I-am anthem laid “a good foundation” for the success he’d experience two years later with “Swingin’.” But don’t dismiss this recording as merely a stepping stone. Anderson’s version of “I’m Just an Old Chunk of Coal” stands as the definitive one, besting strong interpretations by everyone from Johnny Cash and Miranda Lambert to even Shaver’s own. Credit that to Anderson’s distinct warble, which coats the aspiration lyrics in a syrupy amber glaze. He may have been singing about eventually becoming a diamond, but Anderson already sparkled here. —J.H.