The Infinite Verses of Watsky
How Watsky Built a Multimedia Universe — Secret Albums, Book, Doodle Art, World Record, Scavenger Hunts, and His Final Intention Odyssey
If this is your first introduction to Watsky then Welcome To The Family!
In the strange laboratory where slam poetry collides with hip-hop, indie pop, and internet comedy, George Virden Watsky built himself a home. He’s the fast-talking San Francisco kid who became a YouTube meme, then a Billboard charting rapper, then a bestselling author, then the architect of elaborate scavenger hunts.
Now, with his final music project released under a new name — Tommy Designer — the constellation of his career finally looks complete.
I’ve been following him since 2011, long enough that my own story is tangled with his. I’ve hitchhiked across state to catch his meet-and-greets, swapped Pokémon GO invites with his media man, and once handed him a piece of mammoth tusk after reading about his aunt’s narwhal tusk in his book. Following Watsky hasn’t just been about watching a career — it’s been about living inside an expanding universe.
Slam Beginnings
Watsky started as a prodigy in the San Francisco slam scene. In 2006, he seized the Youth Speaks Grand Slam and Brave New Voices International Slam, catapulting him to HBO’s Def Poetry Jam. His early poems — Drunk Text Message to God, Letter to My 16-Year-Old Self, First Time — balanced comedy with honesty, earning him cult status in spoken word circles.
He carried that same duality into his TEDx performances. “Lucky”, performed at TEDxSFED in 2011, broke down privilege with gratitude and wit. Teachers still play it in classrooms.
The Timeline: Virality to Legacy
2006: Wins Youth Speaks & Brave New Voices; appears on Def Poetry Jam.
2009: Releases debut album Watsky.
2011: Uploads Pale Kid Raps Fast — 25M+ views, cementing him as the “fast rapper.”
2013: Drops Cardboard Castles, with collabs from Anderson .Paak (then Breezy Lovejoy).
2014: All You Can Do brings in Travis Barker on drums, peaking at #33 Billboard 200.
2015: Drops Exquisite Corpse with Casal, Anderson Paak, Carmack, Illmac, Recchio, Nocando.
2016: Publishes How to Ruin Everything; contributes An Open Letter to the Hamilton Mixtape.
2019/2020: Complaint and Placement; Guinness World Record freestyle marathon.
2023: Intention ARG release.
2024+: Final project as Tommy Designer.
Viral Stardom
Then came the YouTube explosion. Pale Kid Raps Fast went nuclear, and suddenly Watsky was “the fast rapper.” He leveraged the attention, but never let it define him.
Albums like Cardboard Castles (2013), All You Can Do (2014), and x INFINITY (2016) showcased his balance of humor, storytelling, and raw honesty. His band — Kush Mody, Pat Dimitri, Chukwudi Hodge, and Camila Recchio — became family. Together they were Crème Fraîche, a genre-defying unit.
The Book, Aunt June, and the Mammoth Tusk
In 2016, Watsky published How to Ruin Everything, a New York Times bestselling essay collection. One story described a trip to the Arctic for his Aunt June, who he brought a narwhal tusk home for and she dreamed of finding a mammoth tusk.
That story followed me. At a meet-and-greet in Sioux City, after Ben Glanzer and I hitchhiked there when his car broke down outside Omaha, I handed Watsky a piece of mammoth tusk I had tracked down. He told me Aunt June had already passed away, and even though the friend from the road trip with the tusk, which included Watsky being arrested at one point, mwanted the tusk. Aunt June took the tusk to her grave.
It was no longer just a fan offering. It became a ritual of remembrance.
Hidden Planes, Secret Albums, and Puzzle Hunts
Watsky has a secretive streak. Beyond his public albums are entire “plane” projects — Plane 651, Plane 332, Grain 1,989³³ — hidden on his site under URLs like kisswatskysgluteusmaximus.com. These orphan records are cult artifacts, discovered by fans through riddles and Easter eggs.
In 2023, he pushed the idea to its limit with Intention. Side 2 was locked away until fans solved a global alternate reality game. Nine carved puzzle boxes were buried on six continents, from California to the Bolivian salt flats. Each solved box revealed a track. On April 12, 2023, the second half of the album emerged — a treasure hunt disguised as a record.
Collaboration Constellations
Core band (Free The Biirds): Kush Mody 🎹, Pat Dimitri 🎸, Chukwudi Hodge 🥁, Camila Recchio 🎤.
Poetry roots: Rafael Casal (Blindspotting), Chinaka Hodge (Ironheart), Sarah Kay, Shockwave (beatbox).
Rap peers: Illmac, Nocando, Wax, Dumbfoundead, Taelor Gray.
Producers/musicians: Anderson .Paak, Mister Carmack, Mikos da Gawd, Travis Barker.
Pop culture tie-ins: Hamilton Mixtape, AT&T ad, viral YouTube sketches.
Together, it’s less a feature list than a constellation of careers that grew alongside his.
Family on the Cover
Watsky’s artistry has always been personal, but nowhere is that clearer than on the cover of All You Can Do. He said outright that the album was a tribute to his mother and father. On the front cover is his father, Paul Watsky, photographed as a young man alongside his cat Saruman. The back cover features his mother, Clare Watsky, captured in her own youthful moment. Together, they frame the project in literal family portraits.
For George, it wasn’t only about honoring his parents, but also about channeling the kind of music they loved when they were coming of age. That’s why the deluxe physical edition bursts with psychedelic artwork — a visual callback to the posters and album sleeves of the 1960s and ’70s.
Paul’s influence runs deeper still. A clinical psychologist and published poet, his dual callings echo throughout George’s catalog: humor sharpened by analysis, rhyme that doubles as catharsis. Clare’s activist spirit radiates from the imagery itself. Their fingerprints are everywhere in his discography, whether in the cover art, the cadence of his bars, or the philosophies that hold his songs together.
The Off-the-Record Songs
Outside the official albums lies the lore:
“Swag” — parody brag rap from Guilty Pleasures.
“Mrs. Robinson (Older Ladies)” — his cougar-crush comedy rap over Simon & Garfunkel.
Hall & Oates “You Make My Dreams” cover — pulled for copyright.
“Pumped Up Kicks” freestyle — riff on Foster the People.
Rap GPS video — turn-by-turn directions as rhymes.
“Going Down” video — originally uploaded to Pornhub to bypass YouTube restrictions, featuring uncensored imagery. After YouTube changed its content rules, Watsky re-uploaded it in full.
Mock AT&T commercial — Pale Kid Raps Fast, but for telecom.
These are the Easter eggs of fandom — not on Spotify, but burned into YouTube memory.
Doodles, Drawings, and Margins
Watsky’s lines aren’t only verbal. He doodles compulsively, filling notebooks with surreal faces and spirals. Some doodles became merch — Intention Illustrated paired sketches with lyrics. Others were auctioned off as framed originals during the Complaint/Placement era. At shows, he sometimes signed with a cartoon instead of a name.
The Guinness Record and the Cancelled Tour
In May 2020, during the pandemic, he rapped for 33 hours, 33 minutes, and 19 seconds, setting a Guinness World Record and raising $147,000 for charity. I was proud to be included and called out in his record attempt!
That same year, the Placement tour was cancelled. My wife, Ben and I still flew to Denver, where Hobo Johnson (originally slated to open for Watsky) went ahead with his own show. A strange consolation prize, but still music when we needed it.
Meeting Him Again
By 2023, my wife and I caught him in Minneapolis. His team — especially a guitarist and artist himself, Mike Squires, who has been great on capturing moments on camera over the tours — felt like old friends. Squires and I still trade Pokémon GO gifts, proof that fandom can spill into friendship.
Meet-and-greets didn’t feel like fan service anymore. They felt like reunions.
Tommy Designer: The Final Chapter
In the end, Watsky didn’t just close the book. He turned the page with a new name: Tommy Designer. His final project under that moniker isn’t just a rebrand — it’s a farewell, a capstone on a career that ricocheted from Def Poetry Jam to viral YouTube to Marvel adjacency.
Tommy Designer is Watsky untethered, free to end on his own terms. For those of us who’ve been there since the beginning, it’s both surreal and fitting: the slam poet who hid albums in riddles now hides himself in a pseudonym.
Why He Endures
Watsky has always been more willing to embarrass himself than to fake being cool. That’s why he endures. That’s why fans will hitchhike across Iowa to hand him mammoth tusks. That’s why they’ll dig puzzle boxes out of Bolivian salt flats.
From slam stages to Billboard charts, from doodles to world records, from Aunt June’s tusk to Tommy Designer, the through-line is honesty.
In a world of disposable virality, Watsky built something stranger: a universe stitched from poetry, puzzles, humor, and people who refuse to miss the show.
Epilogue: A Personal Tribute
For me, Watsky’s music has always been more than background noise. It’s been a compass. That’s why I once covered his entire Complaint album as a tribute. It was my way of saying thank you — for the poems, the doodles, the tusks, the tours, the busted cars, the friendships, the meet-and-greets, and the Pokémon friends.
Watsky’s story is still unfolding, even if Tommy Designer is the last chapter. Because his words, like his doodles, are etched not just into paper or beats — but into people.
That’s the kind of record you never stop spinning.