[4] Shortly after this he began writing sketches, and material for other comedians and TV shows and established himself as a regular face on the Irish stand-up comedy circuit.

Following millions of downloads, views and shares across Instagram, TikTok and YouTube he is touring the world with his live standup show while continuing his massively successful Irishman Abroad Podcast series.

[10] After moving home to Ireland in August 2023, Regan's social media content on Instagram, TikTok and Youtube soared in popularity.

[13] Regan wrote and performed sketches on Scope (2007), an Irish science television programme for teenagers and was a regular panellist during the 2008–2009 season of The Panel.

Some highlights from the series included his interview with Chris Rock and Adam Sandler, a series of comedy sketches in which Regan beat toddlers at physical tests of strength and an in-studio game called "The €21 Challenge" in which Regan forced a child to gamble their pocket money in an unusual game of blackjack.

[18] Most of the guests of the more than 350 episodes have been celebrities from the worlds of comedy (Dara Ó Briain, Jason Byrne, Graham Linehan), sport (Sonia O'Sullivan, Richard Hughes), as well as film and television (Jack Reynor, Aidan Gillen, Paul Mescal).

[18] In 2014, Paul Campbell of The Guardian's "Talking Sport" blog wrote of the Jerry Flannery edition that "every single young person reading this should go download this podcast and listen to it every week for the rest of time".