Where were they then?: The Always Sunny ‘Gang’ in the ’90s
When it needed a hook, It’s Always Sunny in Philadelphia appropriated a trendy assessment likening it — or appearing to liken it — to a ’90s gem.
“Seinfeld on crack” has stuck as the de facto tagline for the scrappy, raunchy, persistent digital cable series. Through a demotion from FX to FXX and a couple of planned or unplanned production sabbaticals, Always Sunny has mustered 14 seasons going on 15. Wednesday’s season premiere will punctuate that milestone and end a series-high, pandemic-induced two-year, 11-day gap between new episodes.
At least three more seasons are promised after this one, and as of Wednesday, the show’s run has officially touched three calendar decades.
For the four founding portrayers of “The Gang” running Paddy’s Pub, the show’s inception was an unequivocal breakthrough. And being a mid-aughts start-up starring actors at or pushing age 30, it is a product of a generation that finished its formal education throughout the better part of the ’90s.
In order of their listing in the opening credits, here is a rundown of what each Always Sunny mainstay did between five and 15 years before the show launched. All credits and award nominations and wins are per the Internet Movie Database.
Charlie Day (Charlie Kelly)
Long before his grimy, temperamental alter ego tangled with the Phillie Phanatic, Day spent no small portion of the ’90s chasing a longshot baseball dream.
Growing up in Middletown, Rhode Island, he began the decade one town over as a freshman at Portsmouth Abbey School. There he logged a single acting credit in a production of South Pacific, reserving the rest of his extracurricular energy for athletics. For what it’s worth, when he was a senior in the spring of 1994, he contributed to the Abbey nine’s best season up to that time at 16-1.
Besides his No. 1 sport on the diamond, Day plugged for the boys’ hockey program. The skills he established there reemerged in 2010 when his Always Sunny character coached Mac in shooting.
Before that, Day moved north of the Ocean State border to North Andover, Massachusetts, and walked on to the hardball team at Merrimack College. When that endeavor sputtered after one season at shortstop, he rekindled his fascination with the theater, selecting the small school’s then-newfangled fine arts major.
To round out his ’90s, Day submitted a senior thesis on theater directing, and started inching closer to the mainstream through Boston’s Huntington Theatre and the Williamstown Theater Festival. At the former, he assumed the main role in a production of Dead End.
Glenn Howerton (Dennis Reynolds)
Born in Japan to a military family and raised in assorted domestic and international locales, Howerton had settled into the Southeast by 1990. Over the ensuing decade, he notched his high-school credits in Alabama, and saw action in the state’s annual Shakespeare Festival.
He could have stuck in that state to enroll in Auburn University’s aerospace engineering program, but moved out east to make performing arts his concentration in college and continuing education.
Crediting his parents for greenlighting that choice, Howerton told the Montgomery Advertiser in 2015, “I think the main thing was they told me, ‘If this is something that you are really passionate about, you should give it a shot, because I don’t want you to look back and regret it.’”
After initially enrolling in an arts school within Miami Dade College, Howerton attained an exclusive spot in the drama program at New York City’s Juilliard School. His four years there in Group 29 — opposite Morena Baccarin, Wes Bentley (who left early and soon appeared in Beloved and American Beauty), Wes Ramsey, and Samuel Witwer — spilled over to the winter and spring of 2000, which included a production of Shakespeare’s Love’s Labour’s Lost.
Rob McElhenney (Mac)
McElhenney is the quintet’s only real-life Philadelphian and the only one of Always Sunny’s Gen-X stars who garnered mainstream acting parts in the ’90s.
Upon graduating from Saint Joseph’s Prep in 1995, McElhenney briefly attended Temple University before moving to New York City, where he launched his career. His first genuine head-turner was as accused turned convicted killer Joey Timon on the 1997 Law & Order episode “Thrill.” (His accomplice was played by Home Alone and The Adventures of Pete and Pete alumnus Michael C. Maronna.)
Concomitant with his small-screen debut, McElhenney landed minor movie roles in The Devil’s Own and A Civil Action. In addition, he spearheaded a 1998 Youth Smoking Prevention PSA as a high school student who admitted to trying cigarettes ate age 14 before giving them up out of disgust. Much more exemplary than when Mac and company had Paddy’s circumventing the drinking-age law.
Kaitlin Olson (Dee Reynolds)
Like her onscreen twin brother, Olson had a somewhat nomadic upbringing, although she finished hers where it started in greater Portland, Oregon.
But unlike Howerton’s parents, Olson’s father suggested caution when she expressly sought acting as an undergraduate in the mid-’90s. In a 2017 Portland Tribune feature, Don Olson remembered, “I suggested — a couple of times — that she pursue a second career. Something to fall back on.”
But if anything, she had a foundation springing her forward. The ’90s began midway through Olson’s freshman year at Tigard High School (where she overlapped with future baseball journeyman Mike Kinkade for two years). Per longtime friend and the coincidentally surnamed Heather Olson in a 2006 Tribune article, Kaitlin flawlessly converted rookie nerves during a Tigard production of Rumpelstiltskin.
“She actually had to sing, which she was terrified of doing,” Heather told the Portland paper. She just knocked it out of the park. I think that was a turning point.”
Upon graduating in 1993, and in another distinction from Howerton, she stayed in her home state to complete four years at the University of Oregon. Joining her there, Heather witnessed the snowballing stardom firsthand.
“Freshman year: low profile, got her feet wet,” she said in the aforementioned 2006 story. “By the end she was the lead in everything. She just took over the theater department. It was very clear that was what she was going to do.”
And so, for the final quarter of the ’90s, Kaitlin rode her confidence down the coast to the historic Groundlings troupe in Los Angeles. The resulting credentials led to her first three IMDb credits in 2000, including a small role in another bar-based comedy, Coyote Ugly.
Danny DeVito (as “Frank Reynolds”)
Brought on board in Season 2, DeVito lent Always Sunny a self-explanatory veteran presence. He was a household name before the ’90s, and built on his name recognition throughout the decade through 30 TV, movie, or video-game acting roles.
Nothing in the Paddy’s Pub chronicles evokes that period quite like the overt Seinfeld parody in which Frank is the George Costanza type. Had he stuck to the small screen after breaking out on Taxi in the late ’70s and early’80s, DeVito could have portrayed George for real from 1989 to 1998. Instead he amassed many memorable TV guest spots and movie roles, both before and behind the camera.
To mixed reviews — he earned nods for a Saturn and an MTV Movie Award for best supporting actor, but was also up for a Razzie while some viewers saw anti-Semitic stereotypes in the character — DeVito portrayed the Penguin in 1992’s Batman Returns. As it happens, he revisited that role this year by penning his own comic for the Gotham City Villains Anniversary Giant #1, which is hitting shelves this week.
Sandwiching that big-screen blockbuster, as The Simpsons hit its stride as a revolutionary primetime animated sitcom, he twice voiced Homer’s half-brother, Herb Powell. In the animation/live-action hybrid Space Jam, he was the most prominent heard-but-not-seen cast member as the voice of Swackhammer, then added two more extraterrestrial-themed bit parts in Mars Attacks! and Men in Black.
And barely 10 years before Frank entered the Always Sunny saga, DeVito demonstrated more successful leadership on the film Matilda. Besides salvaging his directing credentials after 1993’s Hoffa yielded another Razzie nomination, he double-performed as the narrator and Harry Wormwood, opposite long-time spouse Rhea Pearlman as Zinnia. The Roald Dahl adaptation nabbed him his first of three Satellite nominations for acting (the others coming the next year for The Rainmaker and a decade later for the third season of Always Sunny).
In terms of team accolades, DeVito joined two SAG contenders for outstanding performance by a cast in 1995’s Get Shorty and 1997’s L.A. Confidential. And while he claimed no hardware, he was a triple nominee at the 1998 OFTA Film Awards for Gattaca, Wag the Dog, and Disney’s Hercules.