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Country music and hip-hop have long vacillated between looking to each other for inspiration and staring at each other warily. Here are 29 examples that run the gamut: Billboard chart-toppers and anthems from insular microscenes; shiny, opportunistic pop collaborations and mud-soaked obscurities; novelty records and sincere simpatico style unions. Each one, in its own way, shifted the idea of what country-rap comity could sound like.

Sir Mix-A-Lot, ‘Square Dance Rap’ (1985)

From “I Just Love My Beat” 12” single

One of the most bizarre conceptual collisions of hip-hop and country was “Square Dance Rap,” a latter-day electro-rap number by Seattle’s Sir Mix-A-Lot, long before “Baby Got Back.” In both versions of the song — the original, and a reworked one on his 1988 debut album, “Swass” — he adopts the rapping voice of a white country boy, and then addresses himself repeatedly as “cotton picker,” an unerringly odd and discomfiting choice.

Rappin’ Duke, ‘Rappin’ Duke’ (1985)

From “Que Pasa?”

An early novelty rap in which the Rappin’ Duke rapped in the screwed-up drawl of John Wayne and was … actually funny. “Two hundred punks, well, what you gonna do?/I got two six-shooters that’ll see me through/That’s 12 dead … and 188 pallbearers.” This is the rare comedy song so skillful it ends up being part of the lore of the genre it was parodying, even rating a mention by Biggie Smalls.

Bellamy Brothers, ‘Country Rap’ (1986)

From “Country Rap”

Little surprise that the first time country music directly nodded at hip-hop was with a lightly arched eyebrow. Bellamy Brothers had been making winking, witty country hits for a decade when they offered this deadpan rural tale — “Neighbor down the road’s got a cow for sale/Twenty dollars more, you get the horns and tail” — that only underscored the throughlines between talking blues, country and rap.

Kool Moe Dee, ‘Wild Wild West’ (1987)

From “How Ya Like Me Now”

The hip-hop cowboy gold standard from a Harlem hip-hop originator who took a song about around-the-way squabbles and, via a video filmed at a Western theme park in New Jersey and enough cowboy hats for the whole crew, remade it as an ominous outlaw fantasy. It was later sampled by Will Smith on his own, far chintzier, “Wild Wild West.”

Intelligent Hoodlum, ‘The Posse (Shoot ’Em Up)’ (1993)

From “Posse: Original Motion Picture Soundtrack Album”

The kickoff to the soundtrack of the black western “Posse” is this history lesson on “black gunslingers” — “One out of every three cowboys were black/But if you watch TV, you’ll never know that” — that name-drops Britton Johnson, the Rufus Buck Gang and others.

Mo Thugs Family featuring Bone Thugs-N-Harmony, ‘Ghetto Cowboy’ (1998)

From “Chapter II: Family Reunion”

“Stop my horse/Whoa, nellyyyyyyyy”: on this full-fledged cowboy fable, Krayzie Bone reimagines himself as a bank robber on the run, bumping into trouble everywhere he goes. He stumbles upon Thug Queen, a horse-stealing, sheriff-killing vagabond, and they team up for adventures out beyond the margins of the law.

Kid Rock, ‘Cowboy’ (1998)

From “Devil Without a Cause”

Kid Rock began his career in late-’80s Detroit as a white rapper at a time when that was still novel. And he pivoted away from hip-hop early as well: “Cowboy” was a rap song with country instrumentation, and it prefigured his wholesale transformation into a pseudo-Southern-rocker who’s left hip-hop all but in the rear view.

Outkast, ‘Rosa Parks’ (1998)

From “Aquemini”

“Rosa Parks,” the lead single from Outkast’s third album, is one of the duo’s deepest and most resonant homages to the long lineage of Southern music — a jubilant blend of fast-blues guitar, porch-stomp percussion and a bridge featuring a turn on the harmonica by André 3000’s stepfather.

Tow Down featuring Big Pokey and H.A.W.K., ‘Country Rap Tune’ (2000)

From “By Prescription Only”

One of the first hip-hop songs to make explicit the thematic similarities between hip-hop and country featured H.A.W.K. and Big Pokey of the Screwed Up Click rapping alongside the white Houston rapper Tow Down, who wore a gigantic belt buckle and bragged, “I’m not Garth Brooks, but I got friends in low places.”.

Wyclef Jean, ‘Kenny Rogers — Pharoahe Monch Dub Plate’ (2000)

From “The Ecleftic: 2 Sides II a Book”

Early in his solo career, Wyclef Jean was keen to show off just how wide-ranging his ear could be. And so on his second solo album came this blend: Kenny Rogers singing his gentle hit “The Gambler” juxtaposed against and interspersed with Pharoahe Monch’s “Simon Says,” with its thunderous “Godzilla vs. Mothra”-sampling beat.

Lil’ Black featuring Willie Nelson, ‘Back on the Road’ (2000)

From “On the Road Again”

Later in life, Willie Nelson would go on to befriend and rap with his fellow marijuana enthusiast Snoop Dogg. But his first appearance on a hip-hop song was alongside the Austin, Tex., rapper Lil’ Black, who recorded regularly at Pedernales, the studio owned by Nelson’s nephew. Lil’ Black wrote Nelson’s quick rap: “I’m rolling in the tour bus, you’re rolling in your Benz/And I can’t wait to get on the road again.”

Nappy Roots, ‘Awnaw’ (2002)

From “Watermelon, Chicken & Gritz”

Throughout the 1990s, Southern rap was coming into its own, but still largely eschewed rural themes. Nappy Roots, who met while in college in Kentucky, developed a style wholly built on them, full of earnest down-home imagery and earthy production.

Bubba Sparxxx, ‘Comin’ Round’ (2003)

From “Deliverance”

“Deliverance,” the second major-label album by the Georgia rapper Bubba Sparxxx, still stands as the high-water mark of country-rap collision. It was a fully realized musical world — on “Comin’ Round,” Timbaland sampled the bluegrass-jam outfit Yonder Mountain String Band for a song that felt intimate and communal all at once.

Moonshine Bandits featuring E-40, ‘Crooked Swerve’ (2003)

From “Soggy Crackerz”

Before country-rap mutated into its own stand-alone cottage industry, rural-identified artists like Moonshine Bandits, a California duo, occasionally found themselves in dialogue with rappers closer to hip-hop’s mainstream. This collaboration finds common ground with Vallejo’s E-40, one of hip-hop’s premier linguists, who politely raps circles around them.

Nelly featuring Tim McGraw, ‘Over and Over’ (2004)

From “Suit”

A dreamy sad-boy duet between the hip-hop melody-maker Nelly and Tim McGraw, one of country music’s premier gentlemen, “Over and Over” became a phenomenon, reaching No. 3 on the Billboard Hot 100. “It ain’t nothing country about this song,” McGraw said at the time — little did he know.

Cowboy Troy featuring Big & Rich, ‘I Play Chicken With the Train’ (2005)

From “Loco Motive”

When the MuzikMafia arrived in Nashville in the mid-2000s, the crew was a sunburst of musical imagination, presenting country music as a big tent, and a big party. This song — the first country-rap song to land on the Billboard Hot Country Songs Chart — was an exuberant blast of fun from a black cowboy rapper and his singing buddies.

Colt Ford featuring John Michael Montgomery, ‘Ride Through the Country’ (2008)

From “Ride Through the Country”

By 2008, the conversation around country-rap had evolved to where a new movement of performers made music that confidently and happily lived on the outskirts of both genres. “We was dirt-road poor and cane-switch raised,” Colt Ford rapped here, on a song that brought casual rap swagger to country balladry.

Big Smo, ‘Honky Tonkin’’ (2010)

From “American Made”

A onetime associate of the white Tennessee rapper Haystak, Big Smo emerged as a promising country rapper in the early 2010s, and eventually even had his own reality-TV show. “Honky Tonkin’” is charming and funny, a friendly celebration of rowdy country nights at the bar where the jukebox is rocking. “Who is that, ol’ Hank?” Big Smo is asked. “Hell naw, that’s me,” he replies.

Jason Aldean, ‘Dirt Road Anthem’ (2010)

From “My Kinda Party”

The original “Dirt Road Anthem” was by Colt Ford and Brantley Gilbert, a sturdy country-rap song that was well-liked but never cracked country’s mainstream. When Jason Aldean chose to cover it, however, he catapulted rapping to the center of the country conversation: His was a No. 1 Hot Country Songs hit, and made it plain that hip-hop was an inevitable — and surprisingly welcome — influence on the genre.

The Lacs, ‘Kickin’ Up Mud’ (2011)

From “Country Boy’s Paradise”

Musically, the Georgia duo the Lacs looked to the past on “Kickin’ Up Mud,” their breakthrough single after a decade of independent releases — crunchy first-wave rap-rock of the mid-1980s, flickers of Miami bass. The rapping is smooth, and the video is exceptionally muddy: “We get riled up when it starts to rain.”

Taylor Swift, ‘Super Bass’ (2011)

Taylor Swift hadn’t made her full pop pivot yet when she stopped in at Nashville radio station 107.5 The River in February 2011. During the interview, she was offered the chance to play a song of her liking, and she chose Nicki Minaj’s “Super Bass,” rapping three bars of it and helping kick-start its pop ascent.

Jawga Boyz featuring Bottleneck and Young Gunner, ‘Ridin High’ (2011)

From “Kuntry”

Another hip-hop anthem about flamboyantly tricked-out vehicles, except here, they’re pickup trucks, and they’re raised up on giant wheels to make them better able to navigate thick, viscous mud. The production is influenced by early Atlanta trap, and the verses — especially Bottleneck’s — are buoyantly fun boasts.

Brad Paisley featuring LL Cool J, ‘Accidental Racist’ (2013)

From “Wheelhouse”

We all make mistakes.

Blake Shelton featuring Pistol Annies & Friends, ‘Boys ’Round Here’ (2013)

From “Based on a True Story …”

If Aldean’s “Dirt Road Anthem” was the song that ensured hip-hop had to be taken seriously on Music Row, “Boys ’Round Here” demonstrated just how adaptable Music Row truly is. Written by three top songwriters and rapped by Blake Shelton, one of country’s biggest stars, it’s brutally efficient, and somehow embraces traditionalist values in radical form. Asked if he knew how to do the dougie, Shelton smarmed back, “No, not in Kentucky.”

Dee Jay Silver featuring Alabama and Nappy Roots, ‘Dixieland Delight (Dee Jay Silver Mix)’ (2013)

From “Country Club”

As the two genres became more and more intimate, a micro-generation of D.J.s emerged who specialized in blending them. Dee Jay Silver toured with Aldean, hosted a syndicated radio show, and released some of his own blends, including this recasting of a country-harmony classic with sharp rhymes from Nappy Roots.

Florida Georgia Line featuring Nelly, ‘Cruise (Remix)’ (2013)

From “Here’s to the Good Times … This Is How We Roll”

The original version of Florida Georgia Line’s “Cruise” was plain but potent — tremendous melody, just a slight sprinkle of rhythm. The remix, however, proved foundational: Nelly delivers an enthusiastic verse, but also clever ad-libs throughout. In the video, he looks euphoric — he knows exactly how effective this hustle can be.

Sam Hunt, ‘Take Your Time’ (2014)

From “Montevallo”

It had to happen: a performer arrived astonishingly comfortable in both idioms, toggling back and forth between them with ease. Sam Hunt’s “Montevallo” was one of the most accomplished Nashville debut albums of the past decade, precisely because it managed — on songs like “Take Your Time” — to apply the most modern and forward-sounding structural strategy to deeply classic songwriting.

Sarah Ross, ‘Shotgun’ (2015)

From “Calm Before the Storm”

Country-rap has one thing in common with the country mainstream: little oxygen for female performers. Sarah Ross sings and raps on this song about exacting revenge on a cheating man — “I was ready to say ‘I do’/Now I wanna cut him every way but loose” — that’s a strong addition to the lineage of done-me-wrong-but-never-again feminist country anthems.

Lil Tracy and Lil Uzi Vert, ‘Like a Farmer Remix’ (2018)

In the identity playground — minefield? — that is SoundCloud rap, this ethereal number predated Lil Nas X’s bold crossover. Lil Tracy is in character here, dreamily rapping about horses and trucks. And Lil Uzi Vert puts on a fake drawl, but just for a few moments — he’s cowboy enough without it.