When discussing the best Macklemore songs, we’re exploring the catalog of an artist who fundamentally changed hip-hop’s independent landscape while delivering some of the most culturally significant tracks of the 2010s. Ben Haggerty, better known as Macklemore, carved out a unique space in rap music by addressing social issues, personal struggles, and celebrating life’s simple pleasures with equal authenticity. His partnership with producer Ryan Lewis created a sonic palette that blended hip-hop with pop sensibilities, indie rock influences, and genuine storytelling that resonated far beyond traditional rap audiences. From Grammy-winning anthems to introspective tracks about addiction and identity, Macklemore’s discography represents a journey of artistic evolution and fearless vulnerability.
Thrift Shop (feat. Wanz)
“Thrift Shop” isn’t just Macklemore’s biggest hit—it’s a cultural phenomenon that dominated 2013 and redefined what independent hip-hop could achieve commercially. The infectious saxophone hook, produced by Ryan Lewis, creates an instantly recognizable foundation while Wanz’s soulful chorus provides the perfect counterbalance to Macklemore’s rapid-fire verses celebrating secondhand fashion. The track’s anti-consumerism message wrapped in an undeniably catchy package demonstrated Macklemore’s ability to tackle social commentary without sacrificing entertainment value, reaching number one on the Billboard Hot 100 and becoming one of the best-selling singles in digital history. The production’s retro vibe and Macklemore’s tongue-in-cheek delivery about “popping tags” made thrift shopping cool again while simultaneously critiquing materialistic hip-hop culture.
Can’t Hold Us (feat. Ray Dalton)
This explosive anthem captures pure, unfiltered energy that translates perfectly whether you’re experiencing it through quality headphones or at a stadium concert. Ray Dalton’s soaring hook elevates the track beyond typical rap braggadocio, transforming it into a universal celebration of ambition and perseverance that transcends genre boundaries. Ryan Lewis’s production builds with cinematic intensity, layering horns, strings, and percussion that create an orchestral hip-hop experience rarely achieved in mainstream rap. The song’s message about unstoppable momentum and refusing to be contained resonated so powerfully that it became Macklemore & Ryan Lewis’s second consecutive number-one hit, solidifying their position as hitmakers who could deliver both commercial success and artistic substance.
Same Love (feat. Mary Lambert)
Few hip-hop songs have sparked as much cultural conversation as “Same Love,” Macklemore’s powerful advocacy for marriage equality released when the issue remained politically divisive. Mary Lambert’s emotionally raw chorus, drawn from her own experiences as a lesbian artist, provides the song’s emotional core while Macklemore’s verses directly confront hip-hop’s historically problematic relationship with homophobia. The track’s piano-driven production creates a reverent atmosphere that allows the lyrics’ weight to resonate fully, avoiding the trap of heavy-handed messaging through genuine emotional honesty. Released during the height of marriage equality debates, “Same Love” demonstrated hip-hop’s capacity for progressive social commentary and earned Macklemore both praise for allyship and criticism from those who questioned whether this message required a straight, white rapper as its messenger—a complexity Macklemore himself acknowledged.
Downtown
“Downtown” represents pure, unadulterated joy—a celebration of moped culture that sounds like a Saturday morning cartoon came to life in the best possible way. The track features an all-star lineup including Eric Nally, Melle Mel, Kool Moe Dee, and Grandmaster Caz, creating a multi-generational hip-hop party that honors rap’s pioneers while maintaining thoroughly modern production. Ryan Lewis crafted a sonic landscape that bounces between funk, soul, and hip-hop with brass arrangements that could soundtrack a New Orleans parade, while Macklemore’s verses paint vivid pictures of urban adventures on two wheels. The music video, featuring Macklemore and crew riding mopeds through city streets in deliberately unhip fashion, perfectly encapsulates the song’s self-aware humor and celebration of uncool coolness that defined much of his appeal.
Glorious (feat. Skylar Grey)
“Glorious” finds Macklemore in reflective mode, celebrating life’s beautiful moments with his grandmother’s perspective providing the song’s emotional anchor. Skylar Grey’s ethereal vocals create a dreamlike quality that perfectly complements Macklemore’s verses about mortality, legacy, and squeezing meaning from every moment we’re given. The production balances electronic elements with organic instrumentation, creating a soundscape that feels both contemporary and timeless, much like the wisdom Macklemore shares about appreciating life before it slips away. This track marked a creative resurgence for Macklemore as a solo artist post-Ryan Lewis partnership, proving he could craft emotionally resonant hits without his longtime collaborator while maintaining the vulnerability and authenticity that always defined his best work.
Good Old Days (feat. Kesha)
Nostalgia rarely sounds as bittersweet and beautiful as it does on “Good Old Days,” where Macklemore and Kesha trade verses about appreciating moments while you’re living them rather than only in hindsight. Kesha’s powerful vocals, delivered during her artistic renaissance following personal and legal struggles, add emotional weight that transforms what could be simple nostalgia into something more profound about presence and gratitude. The production incorporates live instrumentation including piano and strings that create a warm, organic feel contrasting with the electronic elements, much like the contrast between past memories and present reflection. The song’s universal message about recognizing “the good old days” while you’re still in them resonated across demographics, becoming Macklemore’s highest-charting single as a lead artist without Ryan Lewis and demonstrating his continued relevance in an evolving musical landscape.
White Privilege II
Few mainstream hip-hop artists have attempted something as ambitious and uncomfortable as “White Privilege II,” Macklemore’s nearly nine-minute examination of his position as a white artist profiting from Black art forms. The track features contributions from Jamila Woods and addresses complex questions about cultural appropriation, allyship, and the responsibilities that come with platform and privilege in ways that sparked intense debate within hip-hop communities. Sonically, the track shifts between sections, reflecting its multifaceted examination of race, activism, and authenticity, with production that supports rather than overshadows the lyrical content’s weight. While some critics viewed the song as self-indulgent navel-gazing, others appreciated Macklemore’s willingness to publicly grapple with uncomfortable questions about his own success and complicity in systems he criticizes—a conversation that remains relevant in contemporary discussions about race and representation in music.
And We Danced
Before the massive commercial breakthrough, “And We Danced” showed Macklemore’s ability to craft infectious club anthems with personality and narrative depth. The song tells a specific story about a nightclub encounter with vivid, cinematic detail that makes you feel like you’re experiencing the night alongside him, complete with all the awkwardness and excitement of dance floor romance. Ryan Lewis’s production samples Lennon and Maisy’s “Dance Tonight Josephine” in a way that creates a retro-futuristic vibe, blending electronic elements with the sampled vocals to create something both familiar and fresh. This track demonstrated early in Macklemore’s career his talent for storytelling that balanced humor with genuine emotion, creating party music that worked on dance floors while still feeling personal and specific rather than generic club fodder.
Irish Celebration
“Irish Celebration” showcases Macklemore’s cultural pride and ability to craft anthems that celebrate specific communities while remaining accessible to broader audiences. The track’s incorporation of traditional Irish musical elements—including what sounds like accordion and folk melodies—creates an authentic cultural celebration that feels more like a genuine heritage tribute than appropriation. Macklemore’s verses detail his Irish-American identity with specificity and humor, name-dropping cultural touchstones while maintaining the energy of a proper celebration that makes you want to raise a glass and dance. The production balances these traditional elements with modern hip-hop beats, creating a fusion that honors both Macklemore’s cultural background and his primary artistic medium, demonstrating how hip-hop can incorporate diverse cultural influences when done with respect and authenticity.
Otherside
“Otherside” represents Macklemore at his most vulnerable and impactful, addressing his struggles with prescription drug addiction over a haunting sample of the Red Hot Chili Peppers’ song of the same name. The track’s production, built around that melancholic piano loop, creates an atmosphere of reflection and warning that perfectly supports Macklemore’s brutally honest verses about addiction’s grip and the friends he’s lost to substance abuse. This song demonstrated years before his commercial breakthrough that Macklemore possessed the lyrical depth and emotional courage to address serious personal demons without glamorization or deflection. “Otherside” remains essential listening for anyone exploring Macklemore’s catalog because it established the confessional, socially conscious foundation that would define his artistic identity even as he achieved mainstream pop success.
Wings
“Wings” deconstructs sneaker culture and consumerism through Macklemore’s personal history with shoe obsession, starting from childhood desire for Jordans through adult reflection on what those material possessions truly represented. The track’s production builds from minimalist beginnings to a fuller arrangement that mirrors the escalation of consumer desire and eventual disillusionment Macklemore describes in his verses. His storytelling takes listeners through specific memories—saving money for shoes, the social currency they provided, the eventual realization that identity can’t be purchased—creating a narrative arc that transforms a song about sneakers into a broader critique of capitalist culture and self-worth. This track showcased Macklemore’s ability to take a specific, personal experience and expand it into universal commentary, a skill that would serve him throughout his career.
Starting Over (feat. Ben Bridwell)
“Starting Over” documents Macklemore’s relapse after years of sobriety with heartbreaking honesty that few artists achieve when discussing their struggles publicly. Ben Bridwell of Band of Horses provides vocals that add emotional resonance to the chorus, his indie-rock background bringing a different texture that complements Macklemore’s rap verses about shame, failure, and the courage required to begin recovery again. The production maintains a stripped-down quality that keeps focus on the lyrical content, using acoustic guitar and subtle percussion to create intimacy rather than spectacle. This track represents the vulnerable storytelling that has always defined Macklemore’s most powerful work, proving that authenticity and commercial success aren’t mutually exclusive in contemporary hip-hop when an artist commits fully to truth-telling regardless of how unflattering that truth might be.
Ten Million
Before the mainstream explosion, “Ten Million” captured the hunger and ambition of an independent artist grinding toward recognition on his own terms. The track’s production features a driving beat and triumphant horns that create an anthemic quality while Macklemore’s verses detail the DIY approach he and Ryan Lewis took to building their careers outside traditional industry structures. This song became something of a prophecy as Macklemore and Ryan Lewis would go on to prove that independent artists could achieve unprecedented commercial success without major label support. The track’s energy and confidence made it a rallying cry for independent musicians across genres, demonstrating that belief in your craft and willingness to outwork the competition could overcome industry gatekeeping—a message that resonated during hip-hop’s digital transformation.
My Oh My
“My Oh My” pays tribute to Dave Niehaus, the legendary Seattle Mariners broadcaster, creating a deeply personal song about hometown heroes and the voices that define our memories of sports and childhood. The track samples Niehaus’s actual broadcasts, weaving his iconic calls into the production to create a nostalgic soundscape that transports listeners to specific moments in Seattle baseball history. Macklemore’s verses connect his personal relationship with Niehaus’s voice to broader themes about legacy, loss, and the figures who shape our sense of place and belonging, creating a love letter to Seattle that transcends sports. This regional specificity, rather than limiting the song’s appeal, actually strengthens it by demonstrating the power of authentic, place-based storytelling—even listeners with no connection to Seattle baseball can appreciate the emotion and craft Macklemore brings to honoring his hometown.
Dance Off (feat. Idris Elba & Anderson .Paak)
“Dance Off” brings together an unexpected but brilliant combination of talents, with Idris Elba and Anderson .Paak joining Macklemore for a funk-infused celebration of dance floor competition. The production draws heavily from 1970s funk and soul, incorporating live instrumentation that gives the track an organic warmth often missing from contemporary hip-hop productions. Anderson .Paak’s contribution adds his signature blend of singing and rapping over drum breaks that showcase why he’s considered one of contemporary music’s most versatile talents, while Idris Elba’s presence adds star power and genuine musical credibility beyond his acting fame. The song works as both a nostalgic throwback and a modern banger, proving Macklemore’s ability to collaborate across genres and generations while maintaining his artistic identity.
Cowboy Boots
“Cowboy Boots” finds Macklemore in romantic storytelling mode, crafting a narrative about pursuing connection across cultural and lifestyle differences with charm and specificity. The production incorporates country and folk elements—including what sounds like banjo and pedal steel—that create an Americana atmosphere supporting the song’s thematic content about bridging urban and rural identities. Macklemore’s verses paint detailed pictures of a relationship developing despite surface-level incompatibilities, using the titular cowboy boots as a symbol of authenticity and the willingness to step outside your comfort zone for genuine connection. This track demonstrates Macklemore’s range beyond club anthems and social commentary, showing his capacity for storytelling that feels like short fiction set to music—a skill that connects him to hip-hop’s oral tradition while maintaining his contemporary production aesthetic.
Kevin (feat. Leon Bridges)
“Kevin” addresses the opioid epidemic through the story of a specific person lost to addiction, with Macklemore drawing on personal experience to create a devastating portrait of loss and systemic failure. Leon Bridges’s soulful vocals on the chorus provide emotional catharsis while Macklemore’s verses detail Kevin’s story with empathy and specificity, avoiding the abstraction that often characterizes political songs about drug policy. The production maintains a mournful atmosphere with piano and strings that support rather than overwhelm the song’s message about how society fails people struggling with addiction. Released during the height of America’s opioid crisis, “Kevin” demonstrated Macklemore’s continued commitment to addressing social issues through personal narrative, using his platform to humanize statistics and policy debates while honoring someone whose life mattered beyond being a cautionary tale.
Excavate (feat. Saint Claire)
“Excavate” explores the layers we build around our true selves and the work required to uncover authentic identity beneath protective facades. Saint Claire’s ethereal vocals create a haunting atmosphere that perfectly complements Macklemore’s introspective verses about vulnerability and self-discovery, with production that builds from sparse beginnings to fuller arrangements mirroring the excavation process described in the lyrics. The track represents Macklemore’s more experimental, introspective side—the artist willing to get weird and personal rather than chasing radio play or commercial appeal. This willingness to prioritize artistic expression over commercial calculation has always defined Macklemore’s most interesting work, creating songs that reward repeated listening through their production details and lyrical depth.
Light Tunnels (feat. Mike Slap)
“Light Tunnels” addresses mental health struggles and suicidal ideation with raw honesty that makes it one of Macklemore’s most powerful and difficult tracks. Mike Slap’s production creates an appropriately dark atmosphere while Macklemore’s verses detail the specific thoughts and feelings of depression without romanticization or easy answers, offering solidarity to listeners fighting similar battles. The track’s directness about mental health—including specific references to suicide hotlines and encouragement to seek help—demonstrates Macklemore’s commitment to using his platform for harm reduction and community support beyond entertainment. For listeners experiencing similar struggles, having an artist of Macklemore’s stature speak openly about these issues can provide crucial validation and hope, making “Light Tunnels” potentially life-saving art that transcends typical music criticism and evaluation.
Corner Store (feat. Dave B & Travis Thompson)
“Corner Store” showcases Macklemore in hometown hero mode, collaborating with Seattle rappers Dave B and Travis Thompson for a love letter to neighborhood institutions and the communities they anchor. The production incorporates jazz influences and boom-bap beats that feel classic yet fresh, creating a sonic landscape that honors hip-hop tradition while maintaining contemporary appeal. All three artists deliver verses celebrating the corner stores that serve as community gathering places, sources of comfort food, and economic engines in neighborhoods often overlooked by mainstream culture and development. This track connects to hip-hop’s tradition of place-based storytelling while specifically celebrating Seattle’s unique character and the artists emerging from its scene, demonstrating Macklemore’s commitment to elevating voices from his community rather than simply extracting inspiration from it.
Frequently Asked Questions
What is Macklemore’s biggest hit song?
“Thrift Shop” featuring Wanz remains Macklemore’s biggest commercial hit, reaching number one on the Billboard Hot 100 and becoming one of the best-selling digital singles of all time. The song’s infectious saxophone hook and anti-consumerism message resonated globally, selling over 14 million copies worldwide and earning multiple Grammy nominations. The track’s success demonstrated that independent artists could achieve mainstream dominance without major label support, fundamentally changing music industry dynamics. When listening to tracks like this on quality earbuds, you can appreciate the production’s layered details that contributed to its massive appeal.
Did Macklemore win any Grammy Awards?
Yes, Macklemore & Ryan Lewis won four Grammy Awards in 2014, including Best New Artist, Best Rap Album for “The Heist,” Best Rap Song for “Thrift Shop,” and Best Rap Performance for “Thrift Shop.” Their wins sparked controversy when they beat Kendrick Lamar’s “good kid, m.A.A.d city” for Best Rap Album, with Macklemore himself publicly acknowledging he felt Kendrick deserved the award. These Grammy wins represented a historic achievement for independent artists but also highlighted ongoing debates about the Recording Academy’s judgment and potential biases in recognizing hip-hop excellence.
What was Macklemore’s first hit song?
“Thrift Shop” served as Macklemore’s breakthrough hit with mainstream audiences, but within underground hip-hop circles, songs like “Otherside” and “My Oh My” had already established his reputation for thoughtful, personal storytelling. “The Town” from 2007 gained regional success in Seattle, showcasing his connection to Pacific Northwest hip-hop culture. His journey from local Seattle artist to global phenomenon took over a decade of independent releases and grassroots touring before “Thrift Shop” exploded in 2012, demonstrating that overnight success often requires years of preparation.
Why did Macklemore and Ryan Lewis split up?
Macklemore and Ryan Lewis didn’t officially split but decided to pursue individual projects after years of intensive collaboration. Both artists emphasized this was a natural evolution rather than a breakup, with Ryan Lewis focusing on production work with other artists and Macklemore exploring solo artistry on his 2017 album “Gemini.” They’ve maintained mutual respect and left the door open for future collaborations, with both acknowledging their partnership created something special that transformed both of their careers. This approach allowed each artist to grow individually while preserving the legacy of their groundbreaking work together.
What are Macklemore’s most socially conscious songs?
“Same Love” addressing LGBTQ+ equality, “White Privilege II” examining race and cultural appropriation, “Kevin” tackling the opioid epidemic, and “Otherside” discussing addiction represent Macklemore’s most socially conscious work. These tracks demonstrate his willingness to address controversial topics and personal struggles with vulnerability and nuance, often sparking important conversations within hip-hop and broader culture. His approach to social issues—grounding them in personal narrative and specific human stories rather than abstract political rhetoric—has defined his artistic identity and distinguished him within contemporary hip-hop. For those exploring socially conscious hip-hop more broadly, songs from various artists addressing similar themes provide essential listening that demonstrates rap’s capacity for meaningful social commentary.
Is Macklemore still making music?
Yes, Macklemore continues releasing music and touring, with his most recent solo work showing artistic evolution beyond his earlier commercial peak. He’s released multiple projects post-Ryan Lewis partnership including “Gemini” (2017) and “Ben” (2023), exploring more personal themes while maintaining his commitment to honest storytelling. His recent work has received less mainstream attention than his early-2010s breakthrough but demonstrates artistic growth and willingness to prioritize creative expression over commercial calculation. Macklemore remains an active figure in hip-hop, particularly within Seattle’s music scene, where he continues supporting emerging artists and using his platform for social causes.