My Friend Leonard
by James Frey
Mentioned once across 1 show · first heard Feb 2026 on Armchair Expert with Dax Shepard.
The general take
Dax Shepard thinks My Friend Leonard is nearly as good as the original, calling it a beautiful story. He seems to genuinely enjoy it as a follow-up, though the phrasing "almost maybe" suggests it doesn't quite hit the same heights as what came before.
About
Perhaps the most unconventional and literally breathtaking father-son story you'll ever read, My Friend Leonard pulls you immediately and deeply into a relationship as unusual as it is inspiring. The father figure is Leonard, the high-living, recovering coke addict "West Coast Director of a large Italian-American finance firm" (read: mobster) who helped to keep James Frey clean in A Million Little Pieces . The son is, of course, James, damaged perhaps beyond repair by years of crack and alcohol addiction-and by more than a few cruel tricks of fate. James embarks on his post-rehab existence in Chicago emotionally devastated, broke, and afraid to get close to other people. But then Leonard comes back into his life, and everything changes. Leonard offers his "son" lucrative—if illegal and slightly dangerous—employment. He teaches James to enjoy life, sober, for the first time.
Who said what
Dax Shepard👍 Recommends
…recommendation of James Frey's follow-up memoir
“And then my friend Leonard is almost maybe as good, the follow-up. It's a beautiful story.”
Armchair Expert with Dax Shepard — Adam Mosseri Returns (Head of Instagram)at 29:24
Listener reviews
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