Post Malone’s Electrifying 2021 Grammys Performance: A Deep Dive into ‘Hollywood’s Bleeding,’ Style, and Enduring Success

Post Malone, the genre-bending artist known for his unique blend of hip-hop, rock, and pop, capped off another extraordinarily successful year at the 63rd Annual Grammy Awards on Sunday, March 14, 2021. The ceremony served as a powerful victory lap for his critically acclaimed and commercially dominant album, Hollywood’s Bleeding. During the star-studded event, Malone, then 25, delivered a captivating performance of the album’s haunting title track. His arrival on stage was dramatically heralded by a chorus of candle-lit singers, setting a somber yet theatrical tone. Post, clad in an unmistakable leather trench coat intricately adorned with crucifixes, then took center stage, exuding a charismatic presence that held the audience spellbound. His rendition of “Hollywood’s Bleeding” was a masterclass in atmospheric stagecraft, blending his signature vocal delivery with a visually striking aesthetic that perfectly encapsulated the album’s dark yet introspective themes. The performance highlighted not only his artistic depth but also his undeniable stage presence, solidifying his status as one of music’s most compelling live acts.

Malone’s distinctive attire, particularly his crucifix-covered leather trench coat, quickly became a talking point among viewers and on social media, with many drawing comparisons to legendary WWE superstar The Undertaker. The resemblance was uncanny, evoking the iconic wrestler’s signature gothic style and powerful entrance. This comparison was particularly amusing given Post Malone’s prior interaction with the professional wrestling world. In 2018, The Undertaker famously “choke slammed” Post Malone during an appearance, a moment that delighted fans of both music and sports entertainment. Far from being offended, it’s highly probable that Post, a known enthusiast of pop culture and a performer with a keen sense of humor, genuinely appreciated these comments and the playful nod to his past encounter with the legendary wrestler. His willingness to embrace such unexpected comparisons only adds to his multifaceted public persona and his ability to connect with diverse audiences. The theatricality of his Grammy look mirrored the dramatic flair often seen in professional wrestling, creating a memorable moment that transcended typical awards show fashion.

.@PostMalone never disappoints! #GRAMMYs pic.twitter.com/kV25tSOXvE

— Mike Adam (@MikeAdamOnAir) March 15, 2021

Post Malone pulled up like he used to be undefeated at WrestleMania #GRAMMYs pic.twitter.com/rhZ1ErDnsQ

— Slim Shuckle Teaches Typing (@RealSlimShuckle) March 15, 2021

Beyond his compelling performance, Post Malone also made an earlier, unexpectedly viral appearance during the show. He was famously caught on camera enjoying the electrifying, albeit censored, collaboration between Cardi B and Megan Thee Stallion on their hit track “WAP.” With his ubiquitous red cup in hand, Posty’s reaction perfectly mirrored that of countless viewers watching from home. His wide-eyed, slightly bewildered, yet utterly appreciative expression encapsulated the collective amazement that such an unfiltered and audacious performance was unfolding live on broadcast television. This candid moment showcased Post Malone’s relatability and genuine enthusiasm for music, demonstrating that even a superstar can be an excited fan. It became one of the most talked-about and shared moments of the night, further cementing his reputation as an artist who is as authentic and down-to-earth as he is musically talented. His reaction was a testament to the powerful impact of the “WAP” performance and his own unpretentious personality.

POSTY 😂 https://t.co/q3dpMbrgl8

— Complex Music (@ComplexMusic) March 15, 2021

This memorable Grammy appearance arrived almost precisely a year after Post Malone’s last major concert, a highly significant event in hindsight. His show at Denver’s Pepsi Center on March 12, 2020, proceeded as scheduled, marking it as arguably the last large-scale indoor gathering in the United States before the devastating COVID-19 pandemic plunged the country into widespread lockdowns. While Post faced some initial criticism for not canceling the show amidst growing concerns, he admirably pivoted his efforts throughout the subsequent year, transforming what could have been a “lost year” for many into a period of remarkable productivity and philanthropy. He hosted a highly acclaimed Nirvana tribute concert from his home, which garnered immense praise for its raw energy and respectful homage to Kurt Cobain and the band. More importantly, this event raised an astounding over $5 million for the World Health Organization’s COVID-19 relief fund, showcasing his commitment to global welfare. Further diversifying his portfolio, Post launched his own highly successful line of French rosé wine, Maison No. 9, which quickly sold out upon release, underscoring his influence beyond music. He also forged a meaningful partnership with Arnette, an LA-based sunglasses brand pioneering sustainable eyewear, aligning his personal brand with environmental consciousness. Demonstrating his eclectic interests, Post even recorded a spirited cover of Hootie and the Blowfish’s classic “I Only Want To Be With You” as a special contribution to Pokémon’s monumental 25th Anniversary celebration. And now, culminating this eventful year, his powerful performance at the Grammys. For an artist to achieve so much during a year marked by global uncertainty and disruption is a testament to Post Malone’s enduring drive, creativity, and adaptability.

Post Malone entered the 2021 Grammy Awards as a formidable contender, securing a handful of prestigious nominations. His ubiquitous hit single, “Circles,” was recognized in two of the “Big Four” categories: Song of the Year and Record of the Year. Furthermore, his seminal album, Hollywood’s Bleeding, earned a coveted nomination for Album of the Year. Despite the colossal, undeniable success of “Circles” – which spent an astonishing 60-plus weeks on the Billboard Hot 100 chart and even surpassed The Weeknd’s massive hit “Blinding Lights” to become the most played song on U.S. radio for 2020 – it faced an incredibly competitive field. For Record of the Year, “Circles” was up against titans like Beyoncé’s “Black Parade,” Billie Eilish’s “Everything I Wanted,” Dua Lipa’s “Don’t Start Now,” DaBaby and Roddy Ricch’s “Rockstar,” and the explosive collaboration between Megan Thee Stallion and Beyoncé on the “Savage (Remix).” The Song of the Year category was equally daunting, featuring critically acclaimed tracks such as Taylor Swift’s “Cardigan,” H.E.R.’s “I Can’t Breathe,” Roddy Ricch’s “The Box,” and JP Saxe and Julia Michaels’ “If The World Was Ending.” Given the sheer strength and cultural impact of his fellow nominees, Posty, despite his own immense achievements, was widely regarded as somewhat of an underdog for these specific Grammy categories.

However, labeling Post Malone an “underdog” doesn’t diminish his incredible track record of accolades. He had previously swept nine trophies at the 2020 Billboard Music Awards, including the prestigious Top Artist award, demonstrating his undeniable commercial dominance and fan appeal. Yet, at the start of the 63rd Grammys, despite his nine nominations, he hadn’t yet secured a Grammy award, a statistic that felt remarkable for an artist of his stature. This was particularly striking when considering his unprecedented achievement as the first artist to earn three consecutive Record of the Year nominations – for “Rockstar” in 2019, “Sunflower” (with Swae Lee) in 2020, and “Circles” in 2021. This incredible three-peat placed him in an exclusive pantheon of musical legends. According to Billboard, the last artist to achieve such a feat was Steve Winwood, who accomplished it between 1986 and 1988. Before Winwood, Roberta Flack famously managed it from 1972-1974, and the iconic Frank Sinatra set the bar even earlier, from 1958-1961. Post Malone’s consistent presence in such a competitive and historically significant category underscores his profound and sustained impact on contemporary music, regardless of the ultimate Grammy outcome for the 2021 ceremony. His ability to consistently produce chart-topping, critically relevant records solidifies his position as a modern music icon.

Looking ahead, there’s even speculation that Post Malone could potentially achieve a historic four-peat in the coveted Record of the Year category. This optimism stems from his revelation to Complex in October, where he confirmed he was already deep into the creative process for his next album, the highly anticipated follow-up to Hollywood’s Bleeding. He enthusiastically shared, “I’ve been recording a lot of new music for the album. Having the team here with me creating has been amazing. We have been experimenting with some new sounds and are really excited for the world to hear.” This statement ignited anticipation, suggesting an evolution in his sound while maintaining his characteristic artistic integrity. His commitment to pushing creative boundaries is evident in his choice to experiment, hinting at a fresh sonic direction that could surprise and delight his vast fanbase.

Earlier in 2020, as the world grappled with the profound uncertainties of the burgeoning pandemic, Post Malone subtly hinted at the thematic direction of his upcoming project. He conveyed a desire to craft music that not only reflected the collective anxieties and experiences of a COVID-impacted world but also aimed to instill hope and uplift spirits during such challenging times. In a July 2020 interview with the Wall Street Journal, he articulated this artistic mission: “There’s so much to say in these times that will give people hope and hopefully uplift people’s spirits. Because it’s a dark time in America. It’s a dark time in the world. Honestly, for a songwriter to be in the house all day is a blessing and a curse. In the darkest of times, I’m just trying to make something beautiful out of it.” This perspective underscores his role as an artist who seeks to find beauty and solace even amidst global turmoil, promising an album that is both deeply personal and universally resonant.

Expanding on his creative process during lockdown, Post further confided in the Wall Street Journal, revealing how the unprecedented circumstances influenced his artistic output. “To be honest, I think everyone in America is going a little bit crazy sitting at home all day,” he added with characteristic candor. “So I’ve gone a little bit crazy, and I wanted to take more steps outside of my comfort range and make music that I think — to me — is some of the best I’ve made.” This candid admission highlights his willingness to embrace vulnerability and push his artistic boundaries, suggesting that his next body of work will be a deeply personal and potentially groundbreaking exploration of new sounds and themes. His desire to step “outside of his comfort range” signifies an exciting evolution for the artist, promising an album that not only captures the zeitgeist but also showcases Post Malone at his most innovative and authentic.