| 1 | We Insist! Max Roach’s Freedom Now Suite by Max RoachJazz suite on the civil rights movement and Black freedom | 96Full WOKE | Vote |
| 2 | Let’s Get Free by dead prezRevolutionary rap with Black power and anti-capitalist themes | 94Full WOKE | Vote |
| 3 | RBG: Revolutionary but Gangsta by dead prezRevolutionary rap with anti-capitalist and Black power themes | 92Full WOKE | Vote |
| 4 | The Alternate Some Time in New York City by John LennonRadical left remix of the leftist-activist album | 92Full WOKE | Vote |
| 5 | Transgender Dysphoria Blues by Against Me!Punk album on the lead singer's transgender transition | 92Full WOKE | Vote |
| 6 | Dirty Computer by Janelle MonáeQueer-liberation and feminist concept album | 91Full WOKE | Vote |
| 7 | Evil Empire by Rage Against the MachineRadical left anti-capitalist rap metal | 91Full WOKE | Vote |
| 8 | Fables of Faubus by Charles MingusJazz protest piece against segregationist governor Faubus | 91Full WOKE | Vote |
| 9 | Penis Envy by CrassAnarcho-punk feminist album attacking sexism and patriarchy | 91Full WOKE | Vote |
| 10 | Rage Against the Machine by Rage Against the MachineAnti-establishment rap metal; famously left-wing activism | 91Full WOKE | Vote |
| 11 | Revolutionary, Vol. 2 by Immortal TechniqueRadical left rap with anti-imperialist, anti-capitalist themes | 91Full WOKE | Vote |
| 12 | Small Talk at 125th and Lenox by Gil Scott-HeronSpoken-word poems on Black liberation and anti-establishment views | 91Full WOKE | Vote |
| 13 | The Battle of Los Angeles by Rage Against the MachineRadical left anti-establishment rap metal, leftist activism | 91Full WOKE | Vote |
| 14 | Joy as an Act of Resistance. by IDLESPost-punk on immigration, toxic masculinity and anti-Brexit politics | 90Full WOKE | Vote |
| 15 | To Pimp a Butterfly by Kendrick LamarRap album on racism, Black pride and inequality | 90Full WOKE | Vote |
| 16 | A Seat at the Table by SolangeAlbum on Black identity, racism and Black womanhood | 89Leaning WOKE | Vote |
| 17 | It Takes a Nation of Millions to Hold Us Back by Public EnemyLandmark political hip hop on Black power and racial justice | 89Leaning WOKE | Vote |
| 18 | Renegades by Rage Against the MachineCovers album from a famously leftist, anti-capitalist band | 89Leaning WOKE | Vote |
| 19 | Sandinista! by The ClashLeft-wing album with anti-imperialist, solidarity themes | 89Leaning WOKE | Vote |
| 20 | The Revolution Starts Now by Steve EarleAnti-Bush, anti-war protest album by a left-wing artist | 89Leaning WOKE | Vote |
| 21 | The Shape of Punk to Come Obliterated by RefusedAnarchist, anti-capitalist hardcore band, left-wing messaging | 89Leaning WOKE | Vote |
| 22 | Fear of a Black Planet by Public EnemyPolitical hip hop attacking racism and white supremacy | 88Leaning WOKE | Vote |
| 23 | Long Violent History by Tyler ChildersAlbum about white privilege and police violence | 88Leaning WOKE | Vote |
| 24 | Not a Pretty Girl by Ani DiFrancoFeminist folk-rock by an outspoken queer activist | 88Leaning WOKE | Vote |
| 25 | We got it from Here… Thank You 4 Your service by A Tribe Called QuestAlbum on racism and Trump-era politics | 88Leaning WOKE | Vote |
| 26 | Workers Playtime by Billy BraggSocialist folk rock by a prominent left-wing singer | 88Leaning WOKE | Vote |
| 27 | Apocalypse 91… The Enemy Strikes Black by Public EnemyPolitical hip hop attacking racism and the media | 87Leaning WOKE | Vote |
| 28 | Born This Way by Lady GagaPop album with LGBTQ equality anthem title track | 87Leaning WOKE | Vote |
| 29 | Entertainment! by Gang of FourMarxist post-punk critique of capitalism | 87Leaning WOKE | Vote |
| 30 | It’s My Way! by Buffy Sainte-MarieFolk album with anti-war and Native American rights songs | 87Leaning WOKE | Vote |
| 31 | Lemonade by BeyoncéVisual album on Black womanhood, racial justice and feminism | 87Leaning WOKE | Vote |
| 32 | Living With War by Neil YoungAnti-Iraq war protest album attacking the Bush administration | 87Leaning WOKE | Vote |
| 33 | Na Poi / Zombie by Fela Kuti, Africa 70Afrobeat anti-military, anti-authoritarian protest album | 87Leaning WOKE | Vote |
| 34 | Less Talk, More Rock by PropagandhiPolitical punk, anarchist, pro-animal rights and feminist | 85Leaning WOKE | Vote |
| 35 | Diesel and Dust by Midnight OilLeft-wing environmental and Aboriginal rights album | 84Leaning WOKE | Vote |
| 36 | Fresh Fruit for Rotting Vegetables by Dead KennedysHardcore punk satirizing Reagan-era politics and conformity | 84Leaning WOKE | Vote |
| 37 | Pieces of a Man by Gil Scott-HeronPolitically charged soul-jazz on race and injustice | 84Leaning WOKE | Vote |
| 38 | The Clash by The ClashPolitical punk debut with anti-establishment themes | 84Leaning WOKE | Vote |
| 39 | What’s Going On by Marvin GayeSoul landmark protesting war, poverty and racism | 84Leaning WOKE | Vote |
| 40 | Dust Bowl Ballads by Woody GuthrieDust Bowl folk songs by a left-wing, pro-labor songwriter | 83Leaning WOKE | Vote |
| 41 | Black on Both Sides by Mos DefConscious hip hop on Black identity and social issues | 82Leaning WOKE | Vote |
| 42 | By All Means Necessary by Boogie Down ProductionsConscious rap on Black empowerment and anti-racism | 82Leaning WOKE | Vote |
| 43 | Clandestino by Manu ChaoMigrant-rights and anti-border themes, leftist worldview | 82Leaning WOKE | Vote |
| 44 | In the Wind by Peter, Paul and MaryFolk album with civil rights and antiwar songs | 82Leaning WOKE | Vote |
| 45 | Jerusalem by Steve EarleAnti-war post-9/11 album; a song voicing 'American Taliban' John Walker Lindh caused outrage | 82Leaning WOKE | Vote |
| 46 | Kick Out the Jams by MC5Radical left proto-punk linked to White Panther Party | 82Leaning WOKE | Vote |
| 47 | Lives in the Balance by Jackson BrowneLeft-wing album on anti-intervention and social justice | 82Leaning WOKE | Vote |
| 48 | MONTERO by Lil Nas XPop rap by openly gay artist; LGBTQ themes drew culture-war backlash | 82Leaning WOKE | Vote |
| 49 | Special by LizzoBody-positivity and self-love pop; strongly progressive | 82Leaning WOKE | Vote |
| 50 | Survival by Bob Marley & The WailersReggae album on Pan-African unity and anti-oppression themes | 82Leaning WOKE | Vote |