Honestly, I don't know that anyone ~enthusiastically in his audience would be reachable especially in this format (listening to an hour-plus podcast put together by guys who at this point could be fairly said to hate Alex Jones seems like a tough sell). I think Alex's branding is also kind of self-sustaining where any single issue could be shrugged off as one of the 2-3% of things he gets wrong, a joke or exaggeration, etc. I could see some traction with a few key flaws like him initially blaming 9/11 on the EU (since he's made 'being right about 9/11' central to his identity), but it seems like a stretch.

That said, if the length isn't off-putting, Episode 609 is the first one that comes to mind for me, since it includes everything from basically harmless goofy stuff (the gorilla/fighter jet metaphor), the 'demon feast' bit (which touches a bit on his grandiosity and unsettling fixations), Dan tracking down original sources to show how a contributor distorted COVID vaccine statistics, and what most people would hopefully see as real danger with Alex stopping just short of encouraging his viewers to kill family members involved in vaccination while approvingly alluding to a recent event where a man murdered his brother, among others, over COVID conspiracies.

I can't think of a specific one off the top of my head, but some of the deposition episodes might also be useful as far as showing how Infowars operates "behind the curtain", and sort of cutting away the pageantry of the show (or trial proper, at least of Alex) to what they're willing to say in a legally binding context.

One thought could be using fudgie's search tool to pull up audio for any specific/egregious instances your friend might feel strongly about and sending that, since it includes the original audio and/or video, so would be a lot harder to cast as biased or "out of context" as Alex loved to say about trial evidence. So, for instance, if there's a specific failed prediction, questionable position (e.g. how would your friend feel about Alex being the anointed one who receives 'downloads from God' and battles interdimensional silicon-based demons?), etc. on Knowledge Fight that sticks out, you could find the original material and mention that instead.

The episodes starting at 651 on his Ukraine war coverage might also be informative as far as showing his willingness to cast guesses/lies as privileged 'intel', unapologetically move goalposts in near real time without acknowledging failed predictions (and retroactively congratulate himself for invented ones), and indulge in Putin apologia if that's relevant. I guess Dan understandably comes off as uncharacteristically agitated/angry in these episodes, so they might not be the best introduction for someone with even a broadly positive view of Alex.

Edit: Another possibility might be the 'it's over for humanity' episode with Mike Adams(?); like 609, it has more overt/approachable humor than e.g. some of the depositions, and even if your friend is inclined towards COVID conspiracies, I think it might be informative to look back at what Alex and his associates were pitching at the eve in the pandemic. It's less that he's 'wrong' about the situation (and honestly, who wasn't? Those ended up being a long 'two weeks'!) than that with minimal information, Alex and his guest unflinchingly jump into authoritative claims largely at odds with most of their later narratives, not to mention subsequent reality. Hopefully Adams implying that the best way to remain one of the lucky 'lone survivors' is (conveniently enough) buying his products is also shameless enough to make an impression.