Madison worked as a writer for
MTV News and
BuzzFeed in the early 2010s. He has since written for various publications, including
Variety,
GQ Magazine, and
The Daily Beast. Madison was named one of the "most reliably hilarious and incisive cultural critics writing now" by
Nylon in 2016.
Nylon also named Madison to its 2016 list of "The 25 Best Things We Read Online In 2016" for his essay on Donald Trump's political rise. Madison co-hosted a podcast at MTV News with
Doreen St. Félix in 2016 called
Speed Dial with Ira and Doreen, that focused on music, pop culture, and race. In April 2017, Madison was featured in the documentary
The Culture of Proximity. In January 2018,
Crooked Media launched the podcast
Keep It!, a show about pop culture and politics, which Madison hosted with
Louis Virtel until 2025. The show is named for a phrase that Madison coined on
Twitter, which refers to trends, news stories, and other pop cultural phenomena he'd rather not exist. Madison was a writer on the
Netflix series
Daybreak and
Q-Force. He has also written for the show
Uncoupled and the
Quibi original series
Nikki Fre$h. In 2024, Madison appeared in the
Brat Pack-themed documentary
Brats. Madison's debut essay collection,
Pure Innocent Fun, was released by
Random House on February 4, 2025. The book covers various pieces of pop culture from Madison's
adolescence in the 1990s and 2000s. The title is a reference to a quote from
reality television star
NeNe Leakes that has since become a
meme: "It’s unfortunate that people can change something that was just pure innocent fun into drama." On a June 18, 2025 episode of
Keep It!, Madison announced that he would be exiting his position as co-host in late July of that year. Madison's final episode as co-host, entitled "The End of an Ira", was released on July 30, 2025. == Twitter suspension ==