The greatest singer in country history wasn’t known for making great albums. But Cold Hard Truth, the album he cut just before the car crash that nearly killed him, goes on his short list. Jones dances giddily along the thin line that distinguishes “Sinners and Saints,” waters “Our Bed of Roses” with tears of grief, and wrestles with his conscience in both the magnificent “Choices” and the brutal title track. In “When the Last Curtain Falls,” he makes the album’s last word one of forgiveness: for the lover who brought him to his knees and, just maybe, for himself.

The year’s Grammy winner for Best Bluegrass Album, The Grass Is Blue found Dolly Parton joining an all-star cast of pickers (Jerry Douglas, Sam Hunt, Stuart Duncan, etc.) and backing vocalists (including Alison Krauss and Claire Lynch, Patty Loveless and Rhonda Vincent) to embrace a genre she’d grown up with but had never honored so directly. A few swell Parton originals sung in her voice’s husky late-career peak, plus high-lonesome reinventions of songs by Billy Joel and Blackfoot, the Louvin Brothers and Hazel Dickens, adds up to one of the very best albums in Parton’s entire discography. As that’s likely an assessment never previously typed, The Grass Is Blue also probably goes down as the most underrated album in a career we’re still nowhere near to fully appreciating.

Brad Paisley debuted with all of his trad’ bases covered: The comic numbers here about domestic disputes are corny and sly at once, his ballads of romantic loss gather up all kinds of clichés into fresh takes (the title track, for instance, forgoes flipping through a photo album in favor of even more vivid, and painful, memories), and he wraps the album up with both a hot instrumental and a gospel standard. Best of all is “He Didn’t Have to Be,” a post-modern “Mom and Dad’s Waltz”: The son of a single mom, with a family of his own now, pays tribute to the man who became his stepfather.

Their debut, Wide Open Spaces, was the best country album of 1998. So, for an encore, the Chicks naturally released the best country album of 1999, the even better Fly, a celebration of a woman’s equal right to have plenty of self-directed fun. Their “Cowboy Take Me Away,” like Patsy Montana dreaming decades earlier of becoming a “Cowboy’s Sweetheart,” is more about the desire not to be fenced in than about any particular cowboy. “Ready to Run” places women in the commitment-phobic “Free Bird” role for a change (“What’s all this talk about love?”), while the punky bluegrass “Sin Wagon” campaigns for “a little mattress dancin’.” Murder ballad “Goodbye Earl” was probably the most notorious track: Like Slim Shady a year later, the Dixie Chicks’ Mary Anne and Wanda stuff a dead body in their trunk. But unlike Slim’s dead ex, Earl’s murderers come off wholly sane — and justified.

When Kelly Willis first released “Fading Fast,” a co-write with John Leventhal and the title track of a you-should-track-it-down 1996 EP, it was stripped-down and twanged-up. The What I Deserve version, like “I Have Not Forgotten You,” “Heaven Bound” and every other track here, works the other end of the Americana spectrum, riding jingle-jangling guitars, shimmering keyboards, punchy beats, and sunny sing-along melodies. The divide’s a slim one: With ringers like guitarists Chuck Prophet and Mark Spencer chiming behind her, the album’s either a little country-pop masterpiece or a slice of pop-country perfection, take your pick. It went Top 30 on the country album chart, but just like Willis bittersweetly bemoaning her meager luck on the title track, it deserved better.

Granted, Steve Earle’s bluegrass album with the Del McCoury Band doesn’t have the highs of more heralded efforts like Guitar Town, Copperhead Road, or I Feel Alright. But here’s a serious argument: The Mountain just may be the best album in his whole catalog. And “I’m Still in Love with You” ranks among the highest of highs in the catalog of his guest vocalist, Iris Dement, too.

Crossover hit “Single White Female” represents one part of the mainstream Nashville country story in a problematic nutshell. It’s an impossibly catchy ditty of universal domestic desire, but one with its racial and hetero biases right there in the title, sung by a woman who would come out as a lesbian 10 years later. On the other hand, at least 1999 was a year when nearly half of the year’s Number One country singles could be by women. Single White Female, the album, showcases an underrated singer who can sound husky and sweet at once, with a deceptively subtle twang and an ear for great songs. “Why Do I Still Love You,” say, is a gut-punch heartbreaker like something off a George Jones or Patty Loveless album. In “She Went Out for Cigarettes,” Wright heads to the car while her neglectful hubby watches the game. She makes a stop first at the bank, then just keeps going.

The Pilgrim is a country opera that tells a story of love, betrayal, and revenge you’ll swear you’ve heard before. The liner notes avow the tale’s “based on a true story,” but you’ve heard that before too. No spoilers here, but plot points aren’t really the point anyway. After years of chasing what turned out to be only a moderate and sporadic country radio stardom, Marty Stuart shifted his focus toward the modern synthesis of vintage country styles he’s been perfecting ever since: equal parts bluegrass and Bakersfield, Western melodramas and honky-tonk novelties with gospel harmonies, and other old-timey touches that always  country-rock out. Emmylou Harris, Ralph Stanley, and George Jones drop by to share some of their timeless gravitas, and the album concludes with an instrumental go at “John Henry,” where banjo god Earl Scruggs trades licks with mandolin man Stuart looking ahead to his finest role, stanning for tradition in a new century.

Aided by a cloud of friends and other beloveds — Emmylou Harris, Victoria Williams, Steve Earle, her husband Buddy Miller — Julie Miller shares her best songs. Her painfully real voice is present in lyrics and melodies that sing of wind and rivers and rain — a whole wide world, out there — but feel entirely interior. On “I Know Why the River Runs,” she forgoes replaying a phone message in favor of waiting around the house, her forehead pressed against a cold window pane, waiting for a call that doesn’t come. Her “Orphan Train” is like if “People Get Ready” had been transmuted into a Victorian parlor ballad. The title track is a prayer. Throughout, Miller’s cries sound as private and pinched as her husband’s production sounds compressed and front-room cramped. Yet, by some miracle of empathy, her petite voice feels enormous too, chasing fiercely after so many broken others and ushering them safely into her heart, an expansive cathedral.

Retro at its very best. Teaming Mandy Barnett, a one-time portrayer of Patsy Cline, who also just happens to be among the better country vocalists of her generation, with Owen Bradley, Cline’s producer and arguably American pop’s greatest producer, and his A-Team guitarist brother Harold, was a no-brainer. But what’s especially charming is how the varied approaches here serve as a kind of pocket history of the Nashville Sound. Barnett shines not just by channeling Cline at her sultriest, but also by working within the sorts of arrangements that might once have graced crossover country hits by the hyper-twangy Loretta Lynn, the big-pop-voiced Brenda Lee, crooning master Jack Green, and soulful rock & roller Conway Twitty — each a former Owen Bradley collaborator. In other words, I’ve Got a Right to Cry is an apt and poignant tribute to Bradley himself, who passed away before the album was completed.