7 Years 103 days - $iggy Rett$7 Years 103 days - $iggy Rett$
I'm Quitting Alcohol
Comedian David Boyle talks about his friend Miles Wilson, aka $iggy Rett$, tracing his journey from brilliant stand-up comic through years of self-sabotage to a distinctive rap career. The episode mixes raw honesty, wild gig stories and admiration for Miles’s unusual talent and persistence.
10:26•26 Aug 2026
From Comedy Chaos to Rap Phenomenon: The Wild Ride of $iggy Rett$
Episode Overview
- Boyle describes Miles Wilson as a creative "genius" and celebrates his growing recognition as rapper $iggy Rett$.
- The episode recalls years where Miles was, in Boyle’s view, the greatest live comedian he had ever seen.
- Boyle highlights how Miles could win over both hostile bikie crowds and indifferent hipster audiences with sheer presence and improvisation.
- He openly discusses a decade of self-inflicted damage where Miles became "possibly the worst" comedian before finding his place in rap.
- Unique rhyming and playful distortion of language in $iggy Rett$’s songs are praised as something that sets him apart from other artists.
“"We're dealing with something special here, cigarettes is on a different fucking planet."”
You’ll hear Boyle gush with unfiltered pride as he calls Miles "the greatest genius Australia has ever produced" and recalls a stretch between 2012 and 2015 where, in his words, "Miles was the greatest comedian that has ever lived." He paints vivid scenes from brutal gigs: bikie-heavy rooms where other comics "were fucking eating shit" and Miles still "completely fucking annihilates the crowd," then hipster open mics where he pulls out a recorder and has strangers chanting his name within minutes.
Curious about how others handle massive life shifts and creative reinventions? This episode of *I'm Quitting Alcohol* zooms in on comedian David Boyle's long-time mate, Miles Wilson – better known as $iggy Rett$ – and his wildly unconventional path from stand-up genius to cult rapper. Boyle doesn’t shy away from the darker parts either. He talks about "self-inflicted wounds" and a decade where Miles became "possibly the worst comedian of all time" before finding his stride as a rapper.
The tone swings between raw honesty and giddy admiration as Boyle breaks down what makes $iggy Rett$’s music feel so different, including one fan’s comment about rhyming "gun money fronting and bin in the fucking in the one sentence" and Boyle’s cheeky challenge: "Try that Eminem." For anyone interested in how talent, self-sabotage and persistence can all coexist in one chaotic package, this episode offers a fast, funny snapshot.
It’s aimed at people who appreciate brutally honest storytelling, messy journeys, and the strange satisfaction of watching someone finally "pull it off" after years of chaos. You might walk away wondering: who in your life is quietly taking the hardest road to their own version of success?
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