Ep 110: Jamar Gilbert Nominates “Lupe Fiasco’s The Cool” episode artwork

EPISODE · Nov 11, 2025 · 56 MIN

Ep 110: Jamar Gilbert Nominates “Lupe Fiasco’s The Cool”

from This One Goes to 11 · host Tyler Esselman and Michael Osinski

We’ve got school spirit, yes we do, we’ve got spirit, and so does Jamar Gilbert!That’s right, another old school chum joins us this week on the pod and we couldn’t be happier about it. Jamar is an artist of the highest order, a truly gifted actor, and a simply lovely human being in general. I hope each and every one of you gets the pleasure of getting to know this guy at a party some day. He’s the best.And it turns out he has excellent taste in music to boot! Jamar accepted the TOGT11 challenge this week and unearthed for us the mid 00’s conscious rap gem “Lupe Fiasco’s The Cool” by, you guessed it, Lupe Fiasco. A thrilling, 19 track opus, “The Cool” was Fiasco’s “arrival”, if you will. He really put it all together on this sophomore effort and solidified what would be his signature style of intricate rhymes traversing the landscapes of politics, spirituality, and pop culture in a way that few with his level of commercial success in the hip hop space had before. And he could ask for no better champion than Jamar, that’s for sure. Jamar details just how deeply this album affected him as a young man and how it helped him both embrace his own individuality while opening the door to a whole universe of possibilities for what he could become.Our chat with Jamar was everything we love about making this podcast. But will it be enough? Will Mr. Gilbert earn a spot for “The Cool” in the TOGT11 pantheon? We hope you’ll join us to find out.This episode also comes as a playlist on our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.Theme music composed by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Damien Figueras⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.Got a question, comment, or suggestion? E-mail us at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. And follow us on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (@thisonegoesto11podcast). Not to mention our new ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BlueSky⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ account (@thisonegoesto11pod).

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Ep 110: Jamar Gilbert Nominates “Lupe Fiasco’s The Cool”

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