The Cast of Step Brothers: Then & Now

If you’d asked a fan back in 2008 which Will Ferrell comedy would become the most universally liked of the Frat Pack canon, it’s hard to imagine too many saying Step Brothers.

The movie was always well liked, but few could have expected it to outshine the likes of Talladega Nights and Old School on lists like the recent NYT top 250 of the century so far.

It's now 18 years since Step Brothers was released and its starry cast have stayed in our lives in those intervening years, with some growing even starrier than they were before. Let’s check back in for a deeper look at what the Step Brothers cast were up to at that time, what they did next, and what they’re up to now.

Will Ferrell

When Step Brothers was released in 2008, Will Ferrell was at the absolute peak of his powers, delivering smash hit comedies on an annual basis. In the five years leading up to writing and starring in Step Brothers (as lead himbo Brennan Huff), Ferrell had been the main draw in Old School and Elf in 2003, Anchorman in 2004, Kicking & Screaming in 2005, Talladega Nights in 2006 and Blades of Glory in 2007 while still finding time to appear in a bunch of cameos and supporting roles. 

Since then, the monocultural hits have understandably dried up as big screen comedy has moved onto streaming, but Ferrell has still managed to land a significant hit every now and then — like the Daddy’s Home movies or his bit-parts in flicks like The Lego Movie and Barbie. What’s been more impressive is his seamless transition into producing dramas: alongside Adam McKay, Ferrell has helped to bring everything from The Menu and Succession to Todd Haynes’ May December into the world. We thank him for them.

John C. Reilly

When John C. Reilly started making his name playing best pal characters in movies like Days of Thunder and Boogie Nights, few would have expected his mid-career surge as a regular player in mainstream comedy movies. Granted, Reilly was always a bit of a black sheep in that crew, with his only lead role aside from Step Brothers coming in the music biopic satire Walk Hard — a movie that struggled on release but is now considered a cult classic.

More recently, Reilly has been keeping things admirably loose: whether that means playing Oliver Hardy opposite Steve Coogan’s Stan Laurel, popping up in unusual projects like The Sisters Brothers or The Lobster, being an MVP guest star on shows like Tim and Eric, or enjoying the occasional big screen moment in movies like Kong: Skull Island. Regardless of where he pops up, you’re always happy to see him.

Richard Jenkins

For the longest time, Richard Jenkins was one of those guys you always recognised (and were always happy to see) but could seldom remember the name. That all changed in the 2010s after a run of memorable characters in movies like Step Brothers (hilariously, playing Reilly’s dad), Cabin in the Woods and Killing Them Softly, culminated in an Oscar-winning performance in The Shape of Water.

Since then, Jenkins has been trying his hand at more eclectic roles, like in Miranda July’s Kajillionaire, or in DTF St. Louis, or his celebrated turn as Lionel Dahmer in Monster. On the big screen, it’s been a little quieter, but he did re-team with Guillermo del Toro on the under-appreciated gothic horror Nightmare Alley. 

Mary Steenburgen

Mary Steenburgen might only be a little more than a decade older than Ferrell, but she’s played a mother figure to him now on two occasions: as his stepmother in Elf and as his actual mom in Step Brothers. The ageless star (who’s been married to Ted Danson since 1995) began acting in the 1970s, won an Oscar for Jonathan Demme’s Melvin and Howard in 1981, and became a bona fide movie star after playing Doc Brown’s love interest in Back to the Future III.

More recently, Steenburgen has been enjoying the spoils of late career fame, frequently appearing as herself in Curb Your Enthusiasm and embracing her inner wine mom as one of the central foursome in the hugely successful 2018 movie Book Club. Her most recent role saw her playing pickleball opposite Jake Johnson in The Dink.

Adam Scott

Of all the stars to appear in Step Brothers, Adam Scott (who plays Derek, Brennan’s douchey younger brother) is probably the one you would best describe as being at the beginning of his journey when the movie came out. He’d already had small roles in The Aviator and Knocked Up, but 2009 was when things really started to happen for him.

First up came his starring role in Party Down, a show that was canceled after two seasons (it was recently revived) but was beloved to anyone in the know. Regardless of that cancellation, that role led to an even bigger one as Leslie Knope’s nerdy love interest in Parks and Recreation and the rest, as they say, is history. 

Nowadays, Scott is best known for Severance, but recent roles in movies like Hokum suggest that we could be in store for Scott’s horror era.

Kathryn Hahn

After lighting up the MCU’s sometimes uninspired TV offerings with her performances in Wandavision and Agatha All Along, it’s fair to say that Kathryn Hahn has never been more popular, but longtime Hahn-stans will know that that recognition was long overdue. 

In the early ‘00s, the actress started making her name with a string of supporting roles — usually as the girlfriend or best friend type in romantic comedies like How to Lose a Guy in 10 Days or The Holiday — both of which, incidentally, she got to do in Step Brothers: as the wife of Derek and the lover of Dale.

That all changed in the mid-2010s thanks to her remarkable turns in Transparent and Tamara Jenkins’ Private Life — since then, the sky’s been the limit. Keep an eye out for her presumably unhinged turn in the live-action Tangled in 2028

Rob Riggle

Nobody with a name like Rob Riggle should be allowed to do anything but be a comedian. Thankfully, the Step Brothers star (he plays Derek’s best friend and work colleague, Randy) is one, and a damn funny one at that, especially when it comes to playing arrogant bro types.

Riggle got his foot in the door in the comedy world through his appearances on Conan and The Daily Show before moving into movies as a reliable bit-player in Ferrell’s crew. On the big screen, you can see him in Talladega Nights, The Internship, and The Hangover, to name just three, but he’s really best known for his wide ranging work on TV, appearing over the years in everything from Brooklyn Nine-Nine and Key & Peele to Curb and The Simpsons.