For more than a century, the evolution of popular music has delivered stark parallels to Western society's own progression. One could even say that popular songs and styles partake in a tangible feedback loop, simultaneously responding to and informing cultural shifts. In turn, the best tunes make either purposeful or inadvertent statements about the era in which they're being recorded and released. Some of those statements, meanwhile, never lose their ability to resonate. Perhaps this is why songs like “We Shall Overcome” continue to be used as a rallying cry against oppressive forces.

Because music has the unique ability to both run with and shape the cultural tide, history's most groundbreaking works are often its most controversial as well. In the 1920s through the 1940s, songs of poverty, racism, and hard labor threatened to undermine various institutions of authority. That was followed by genres such as rock ‘n' roll and funk, which respectively enhanced the growing divide between young and older generations. Jump ahead decades and popular music is still influencing fashion statements, attitudes, and perspectives alike, sometimes within the same hit single. And someone is almost always angry about it.

Today, Stacker celebrates history's most boundary-pushing—and thereby controversial—songs. Taking a broad approach to the concept, Stacker selected musical milestones that either explored controversial subject matter or literally sparked controversy. To compile the list, Stacker scoured Billboard charts, music and album reviews, news articles, and primary documents found online. The resulting compilation includes protest songs, sociopolitical commentaries, scandalous music videos, and tunes that just plain rubbed people the wrong way. Each example provides a sonic document of society's past, while a few go to show just how little certain things have changed since the time they were recorded.

A brief disclaimer: Old music can be a slippery entity and some of the songs on the list were recorded or released well before they rendered any sort of impact. Along similar lines, many protest songs were written and performed by one artist and then passed down to others in the folk tradition, hitting the mainstream somewhere along the way. As a result, some entries might be best described as approximations with regards to when the song caused a stir or tackled a specific theme. Without further delay, here are controversial songs from the year you were born.

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Artist: Fats Waller

Featuring lyrics like “my skin is my only sin,” this song of lament was originally composed for the musical revue “Hot Chocolates.” It was subsequently popularized by jazz legend Louis Armstrong, who recorded several versions throughout his career. Ralph Ellison also mentioned the song in the prologue to his seminal novel about race in America, “Invisible Man.”

Artist: Lowe Stokes

America was in the midst of Prohibition by 1930, but that wasn't going to stop fiddler Lowe Stokes from getting his illegal drink on. He sings about guzzling moonshine in the mountains of Georgia, and then predicts that the ban on alcohol will be lifted by 1933. As it turned out, his prediction was right on the money.

Artist: Cab Calloway and His Orchestra

This jazz record was so successful that it continues to inspire bellows of “Hi De Hi De Hi De Ho” almost 90 years later. Moving beyond its most nonsensical and enduring line, the song is laden with cleverly concealed drug references. Words like “kokey” and phrases such as “kick the gong around” pertain to cocaine and opium, respectively.

Artist: Bing Crosby

At the height of the Great Depression, E.Y. Harburg and Jay Gorney wrote this provocative anthem for a musical revue. When crooner Bing Crosby delivered his take, it became the best-selling record of its time. In the song, a beggar addresses the nation that took his job and shattered his dreams.

Artist: Ginger Rogers (and chorus)

Despite its timeless catchphrase and upbeat melodies, this classic song and its somewhat controversial title emerged from a grim economic landscape. Recorded by Ginger Rogers and a chorus for the musical “Gold Diggers of 1933,” it tells “Ol' Man Depression, you are through, you done us wrong!” A slew of hit cover versions would follow.

Artist: Unknown

Facing overtime hours without extra pay, textile workers across the Southern states in 1934 went on strike. In Winnsboro, S.C., this song of protest and hardship emerged from the movement. Popular artists like Pete Seeger and Lead Belly would later record their own versions.

Artist: Cleo Brown

Famous jazz and blues vocalist Cleo Brown dreamed of a more inclusive Hollywood back in 1935. Singing over a catchy piano riff, Brown imagines legions of black performers heading westward in pursuit of fame and fortune. The song's upbeat vibe does little to mask the harsh racial realities of its time.

Artist: Stuff Smith

Cult film “Reefer Madness” was released the same year as this catchy jazz song, which took a far less precautionary approach. Using the parlance of the times, Stuff Smith and his Onyx Club Boys describe the life of a “viper,” or an underground pot-smoker. Fats Waller later recorded his own version under the name of “The Reefer Song.”

Artist: Harold Rome

Composer Harold Rome wrote this tune for “Pins and Needles,” a hit musical that starred real-life garment workers and took a pro-union stance. Rife with reactionary overtones (hence the name), the song was sure to make a few millionaires squirm in their seats. In 1962, Barbra Streisand performed a rendition for the show's 25th-anniversary studio recording.

Artist: Lead Belly

After experiencing hostile segregation during a trip to Washington D.C., Lead Belly did just what a great blues singer would do: he wrote a song about it. Like an early ancestor to viral media, it spread awareness of the privileged elite and their racist practices. Due to the song's political associations, Lead Belly was reportedly invited to perform it at socialist summer camps.