Rise to Fame
That '80s Show lasted 13 episodes before Fox cancelled it in 2002. The paycheck Howerton got from that gig reportedly paid for the camera he and Rob Mac and Charlie Day used to shoot the Always Sunny in Philadelphia pilot for about $200. FX picked it up in 2005, and what started as three broke actors making a calling card became the longest-running live-action American comedy in history. He built Dennis Reynolds over 18 seasons into a narcissist who's escalated from merely terrible to actively sociopathic, and plays every bit of it completely straight.
In the Spotlight
Always Sunny has been critically beloved since 2005 without ever earning Howerton a single Emmy nomination. BlackBerry in 2023 finally made the industry look twice. He played Jim Balsillie, the volatile co-CEO of RIM, won at the Hollywood Critics Association and Toronto Film Critics Association, and was broadly seen as an Oscar snub. The real Balsillie called the performance 'almost entirely fictional' and 'brilliant' in the same sentence. Always Sunny is now in Season 18 and the Emmys still aren't calling.
Side Notes
He was born in Okinawa to an Air Force fighter pilot, grew up in England and South Korea before landing in Alabama, and was headed to Auburn for aerospace engineering before pivoting to acting. He made it to Juilliard, worked as a Manhattan bellhop to cover rent, and graduated in 2000. The ADHD diagnosis came at 47 in 2023. Given that Dennis Reynolds is essentially a walking DSM entry with a superiority complex, the timing may explain more about the character than he intended.