Representative records from the current filtered evidence set.
Strongest Signal
Ira Madison III served as the creator and primary host of Keep It , a podcast produced by Crooked Media from 2018 to 2025. Crooked Media was founded by former Obama administration staffers with an explicit mission to provide a progressive…
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Through his work at Crooked Media and his podcast, Madison has regularly collaborated with and interviewed prominent anti-MAGA figures, including Jon Lovett , Jon Favreau , and various Democratic politicians and activists.
Strongest Not MAGA
In a guest column for The Hollywood Reporter, Madison criticized Ellen DeGeneres for her defense of Kevin Hart, framing the issue within the context of toxic messages to the Black LGBTQ community and broader social accountability, a stance…
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Madison's career is defined by contributions to outlets with strong progressive editorial stances, including The Daily Beast, GQ, and MTV News, where his work often intersected with political commentary critical of the Republican party.
While writing for these outlets is not a direct political act, the consistent choice of platforms that are editorially opposed to MAGA narratives reinforces his alignment.
He has also written for GQ, Harper's Bazaar, New York, and Interview among other publications.
Madison has frequently used his platform to criticize celebrities who remain neutral or fail to oppose Trump-era policies, arguing that pop culture is inherently political and that silence is a form of complicity.
Notes: This is a recurring theme in his 'Keep It' podcast monologues.
This 'silence is complicity' stance is a hallmark of the anti-MAGA cultural movement, pushing for active resistance rather than neutrality.
Ira Madison III is the author of the nationally best-selling Pure Innocent Fun: Essays, called 'a brilliant critical voice'...
Through his work at Crooked Media and his podcast, Madison has regularly collaborated with and interviewed prominent anti-MAGA figures, including Jon Lovett, Jon Favreau, and various Democratic politicians and activists.
Professional association with the 'Pod Save America' founders and the broader Crooked Media ecosystem reinforces a career-long alignment with anti-MAGA political infrastructure.
Lovett or Leave It Live in DC: Tickets available now... Keep It 423 Episodes
In his Substack 'Frank,' Madison has explored themes of masculinity and fantasy in the context of modern culture, often contrasting progressive views on gender with traditionalist or 'manosphere' narratives frequently associated with MAGA-adjacent cultural movements.
Notes: Date reflects recent archive activity.
Madison's intellectual output consistently challenges the cultural foundations of the MAGA movement, particularly regarding gender and social hierarchy.
Are Men “So Back?” On masculinity, fantasy, and Heated Rivalry
Madison has been a vocal advocate for Black representation and the 'Black Renaissance' in Hollywood, writing extensively on how institutional structures (often defended by conservative/MAGA rhetoric) have historically excluded Black success.
His focus on systemic racism and institutional reform aligns with the progressive opposition to MAGA's 'anti-woke' and 'anti-DEI' policy platforms.
Issa Rae Knows Hollywood Wasn’t Built for Black Success—but, Well, F*ck That
In a guest column for The Hollywood Reporter, Madison criticized Ellen DeGeneres for her defense of Kevin Hart, framing the issue within the context of toxic messages to the Black LGBTQ community and broader social accountability, a stance aligned with progressive cultural critiques of the MAGA era.
This demonstrates Madison's active role in progressive cultural criticism, specifically focusing on intersectional issues (race and LGBTQ+ rights) that are frequently points of contention with MAGA-aligned cultural views.
Ellen DeGeneres’ Kevin Hart Interview Was an Insult to the Black LGBTQ Community... sent a toxic message to the black LGBTQ community.
Ira Madison III served as the creator and primary host of Keep It, a podcast produced by Crooked Media from 2018 to 2025. Crooked Media was founded by former Obama administration staffers with an explicit mission to provide a progressive counter-narrative to the MAGA movement.
Notes: Crooked Media is widely recognized as a leading liberal media organization.
Madison's central role in a media company founded specifically to oppose the Trump administration and mobilize progressive voters is a high-weight indicator of anti-MAGA alignment.
From 2018 to 2025, he served as the main host of the Crooked Media podcast Keep It!
Ira Madison III is the host of Crooked Media’s pop culture podcast Keep It.
Madison has frequently critiqued the intersection of celebrity culture and politics, including a 2017 piece titled 'What Is Katy Perry Doing?' which analyzed the effectiveness of 'woke' branding during the early Trump era, often expressing skepticism toward performative activism while maintaining a progressive baseline.
Madison's work consistently engages with the political climate of the Trump era from a critical, left-leaning perspective, even when critiquing his own side's tactics.
What Is Katy Perry Doing? Ira Madison III May 26, 2017