The Transformation Of Kat Dennings From 9 To 35 Years Old

Everybody loves a good glow up. And though her aesthetic has maintained the same striking, gothic sensibilities as when she was younger, the transformation of Kat Dennings from childhood to adulthood has nonetheless seen the star embracing her power, flourishing in more polished looks, and flexing her professional success in increasingly fabulous ways. A proud Hollywood outlier, Dennings once proudly referred to herself as "a weird one" while in conversation with GQ and suggested that her obsessive nature and love of "weird influential movies" might have something to do with that. Whatever the reason, Dennings has (thankfully) never changed herself for an industry which can all too often demand its women fit particular looks, personalities, shapes, and sizes. Throughout her career, the actor has experimented with her looks and performances, but has never compromised who she is for it. 

On the red carpet, this is embodied by the old-school Hollywood glamor that Dennings has repeatedly leaned on to celebrate her curves. Speaking to InStyle, she suggested that her love of vintage looks came from trying on dresses "from the 1940s and 1950s" and discovering that they fit her "curvier shape" perfectly. "I figured out in that moment, 'Fine, I belong in this style. It feels like I am included in this.'" And she has been ever since. 

Have your sharpest and most deadpan quips at the ready — and for the love of goth, assume your most dramatic, black-clad pose — because this is the transformation of Kat Dennings from 9 to 35 years old. 

Kat Dennings and her Addams Family values

Like many of Tinseltown's finest, Pennsylvania native Kat Dennings spent her entire childhood vying for stardom. As she explained to Backstage, she was "that kid who just wouldn't stop hounding her parents to let her try acting," but mom and dad wouldn't let her give it a go until she was "nine and a half." The family didn't have the bank to be throwing cash at acting lessons for the young star-in-the-making. Instead, she did the "thing of learning as you go."

She told Backstage she subsequently "paid her dues" starring in a bunch of commercials, or clocking in "triple overtime" as an acting extra, which might explain her delightfully unique acting style which feels naturalistic and effortlessly droll. But her childhood would also help to shape her distinctive public persona too. As she related to Philadelphia, she "basically grew up in the woods" which she credits as to why she's "so socially weird" as an adult.

What's more, as she said in an interview with AV Club, she "grew up in a haunted house" and was essentially "raised by ghosts." Evidently, she embraced the spooky vibes. As  Dennings said on a 2014 episode of "Conan," she was something of a goth kid who was "very dramatic" and "obsessed with 'The Addams Family'" to such a degree that she'd often tell people her name was Wednesday and sleep with her arms crossed like the character — which is a relatable origin story for every overgrown goth.

A guest spot and the city launched Kat Dennings' career

After landing commercial after commercial, Kat Dennings finally scored her first TV role as a precocious pre-teen who hires Kim Cattrall's Samantha to plan her bat mitzvah on "Sex and the City." As she told Backstage, it was the role that gave her the opportunity to move to Los Angeles with her mom. And once they got there, she never left. 

Though the HBO dramedy was a huge hit, Denning told The Hollywood Reporter her family "didn't have cable" and subsequently "had no idea what the show was." The actor noted that on reflection the role "was obviously really inappropriate for me at that age," though it's arguably this aspect which only highlighted Dennings' burgeoning talent. Her performance was wise beyond her years, and her depiction of a catty, bratty teenager showcased a wit which managed to maintain pace with that of an acting powerhouse like Cattrall. 

Thus, a star was officially born. In the years to come, Dennings would spend her teens continuing to oil her acting training wheels with Hollywood-starter-pack roles in things like "Without a Trace," and "CSI: Crime Scene Investigation," and a single season of the short-lived sitcom "Raising Dad," in which starred opposite Bob Saget and future Marvel Cinematic Universe gal pal Brie Larson. Sure, it got cancelled, but it didn't matter — she was on the verge of bigger things.

Kat Dennings broke into the Tinseltown big leagues

By the time she'd turned 18, Kat Dennings had finally landed the big screen hit she deserved, playing a hormonal angsty teenager desperate to lose her virginity in Judd Apatow's "40 Year-Old Virgin." As she recalled to The Hollywood Reporter, the project was "such a cool film to be in" especially because it was the "first ... big thing" for many members of the cast and crew, including herself. The film demonstrated Dennings' incredible comedic flair, with the bonus of being a huge hit. 

But there was more to her performance than simply clowning. Her co-star Catherine Keener — who played her long-suffering mom in the movie — praised the young star's rare talent to The New York Times Magazine. "From the beginning, Kat had her own rhythm," the Oscar-nominated actor said, "a way of being funny and emotional at the same time." Keener also perfectly outlined what sets Dennings apart from other young starlets: "She's comfortable being different."

"40 Year-Old Virgin" gave Dennings her first proper taste of the red carpet, on which the actor highlighted her natural beauty in low-key looks which flirted with rebellion against conventional glamor rules. The star would pair sensible, professional dresses with bold makeup choices which echoed that of punk star Brody Dalle's signature bruised eyes and red lip combo. She was a Hollywood celebrity for whom every alternative teenager could confidently claim as their own. 

Paging Kat Dennings

After establishing herself as a star to watch out for on the big screen, Kat Dennings continued to flex her skills on the small screen in "ER." The actor enjoyed a super dramatic arc typical of the primetime soap in which she depicted an underage teenage girlfriend of Shane West's Dr. Ray Barnett, who later has to be saved from her violent father.

Speaking to The Hollywood Reporter, Dennings shared that on top of "how cool" the experience was of being on the Warner Bros. set with "a whole hospital in it," she was also extremely hyped to be acting alongside such an amazing cast. "At the time 'Bend It Like Beckham' was my favorite movie," she said, "and I was so excited to be on the same show as Parminder Nagra." Clearly, she was in her element and it reflected in her newfound sense of style. 

While Dennings pivoted further into her goth roots with striking makeup and style choices, her preference for old school glamor also become more evident in the impeccable manner she began to wear her signature bold red lip — something which she confessed to Yahoo! News makes her face feel "weird" whenever she doesn't wear it. "I hate to be predictable," she said, "but I think Marilyn Monroe put that seed in my head that red lipstick equals glamour and confidence." As her star continued to shone brighter, so too did her experiments with style. 

Cookie cutters are of no use to Kat Dennings

Marilyn Monroe may have been a predictable muse for Kat Dennings to draw inspiration from, but there's no denying she was an ideal one. As she turned 21, the star begun to really elevate her style with full vintage throwbacks which teased the beginnings of some of her signature style accents: One-shoulder dresses and décolletage cut-outs paired with a dash of va-va-voom and pencil shapes — all of which perfectly honored her bombshell figure.

It's telling that at a time when she appeared to be really defining her style, she was also really taking helm of her career by starring in the indie comedy "Charlie Bartlett." The film was the first major opportunity for Dennings to lead a movie, which she did alongside the late Anton Yelchin. It was an ideal vehicle for the star on many levels: "Charlie Bartlett" is an extremely sweet teen flick with a weirdo, oddball edge to the main characters. Notably, it also has a throwback '80s vibe which Dennings noted to Rotten Tomatoes felt "completely different" to the "teen stuff" of the time. 

At this stage in her career, it was evident that the actor didn't fit into the conventional cookie cooker shape often associated with Hollywood up-and-comers. But by all accounts, she thrived exactly for this reason, not in spite of it.  As she continued her ascent, this would become her unique selling point.

Kat Dennings became an 'indie hipster darling'

In 2008, Kat Dennings was what publications like The Playlist were hyping up as being "the cute up-and-coming indie hipster darling" — a position conclusively assured by her turn in the alternative musical rom-com "Nick & Norah's Infinite Playlist" alongside fellow indie darling Michael Cera.

The film was well received, but ultimately it also proved to be a joyful personal turning point for Dennings. She told The Hollywood Reporter that she and the cast had a blast making the flick in New York. "What you're really watching is the best autumn of all those kids' lives," she said, "we had the best time, all of us." While Dennings kept her look within the vintage goth realm, she did show up to "The House Bunny" premiere in soft pink — yes, pink — lipstick.

On top of writing a screenplay with her brother which landed on the esteemed Black List in 2008 (via Deadline), the star also auditioned for a role in Tim Burton's "Alice in Wonderland." Sadly, nothing further came of the screenplay and her role eventually went to Mia Wasikowska, a decision which "devastated" Dennings at the time. She told Glamour, "I think that might've been the only role I cried over losing."

Success sure suits Kat Dennings

Having starred alongside Marvel maven Robert Downey Jr. in "Charlie Bartlett," self-proclaimed "huge comic book fan" Kat Dennings told Rotten Tomatoes that she'd "flip out" to be in a superhero movie, though she raised her concerns that she's "a bit short" to play one. Prior to entering the MCU, Dennings had a chance to enjoy her first taste of superheroes with the dark indie film "Defendor," in which she played a sex worker saved by Woody Harrelson's DIY superhero. 

Though she, as she said in Collider, "went bananas" for the role and continued her indie film credits with a turn in romantic drama "Daydream Nation," her further sartorial refinement — which had evolved to incorporate more contemporary styles and pieces — could have been interpreted as an attempt to manifest more mainstream success via her overall look. 

Whether that was her intention or not, by 2010 she'd officially been cast in Kenneth Branagh's "Thor" in an unspecified role. It was an achievement so big for the star that she told Collider that her anticipation for it was comparable to "when little kids know they're going to Disneyland and they ... start counting down the days." It's worth noting that this was before Marvel got bought by the House of Mouse — so on top of being able to manifest her own destiny, Dennings may have also had some powers of prescience too. 

Hammer time and a hit series for Kat Dennings

Kat Dennings entered her mid-twenties as comic relief in 2011's "Thor." As Slash Film noted, fans attempted to guess what classic Asgardian character she could play — the seductive sorceress Amora, maybe? Or Hela, the goddess of death? — but the actor instead depicted deadpan poli-sci intern Darcy Lewis. Which was arguably a minor victory for scientists everywhere who fantasized that a Chris Hemsworth type could somehow be involved in their research assignments. 

Impressively, Dennings' character wasn't in the comic books but was instead "born out of my imagination," as the actor told Starry Mag. Initially penned as being a minor part of the film, Darcy was so "well received" during the initial table read that her role "just got bigger and bigger" (via Daily Actor). Her filmography was getting bigger and bigger, too: The same year "Thor" hit theaters, CBS launched the sitcom "2 Broke Girls." 

Executive produced by "Sex and the City" head honcho Michael Patrick King — who confessed to GQ that he wrote the role specifically for Dennings who he praised for having an "amazing outsider edge" — "2 Broke Girls" tied a bright shiny bow onto the star's mainstream breakthrough year. So, what else could a girl do but flex? Dennings strutted red carpets in high voltage looks that served major body-ody-ody without apology. Her career had blown up — and her makeup, style, and hair perfectly followed suit. 

Marvel maven Kat Dennings maintains her indie vibe

Blessing red carpets everywhere with her looks, Kat Dennings continued to showcase her dramatic, outsider style alongside her newfound proven star power. The result was a heightened sensibility for decadent couture and a return to her favored bold red lip. On screen, the star reprised her role as Darcy Lewis in "Thor: The Dark World" and "2 Broke Girls" became the new anchor show for CBS' successful Monday night comedy block (via Variety).

On the surface, both projects could be considered successful, but was there more to the story? While starring in any Marvel film is a huge deal for any actor, the "Thor" sequel is one which continues to be scrutinized by fans as one of the "least-loved" of the first phase, as Digital Spy put it. Meanwhile "2 Broke Girls" was suffering from a slew of audience complaints regarding the show's perceived vulgarity (via The Wrap) made worse by dipping ratings (via TV Line). 

But hey, that's showbiz. And no negativity was enough to detract from Dennings' wicked star power as she proved by starring in horror comedy "Suburban Gothic" from oddball indie filmmaker Richard Bates Jr. As well as starring opposite former boyfriend turned good pal Matthew Gray Gubler (via Shockya), the actor also got to enjoy gothing it up a storm opposite King of the Outsiders, John Waters. Who even needs to impress the mainstream when you've got weirdo kudos like that?

Goth girl Kat Dennings meets a clean-cut crooner

While "2 Broke Girls" floundered slightly in its third and fourth seasons, Kat Dennings nevertheless thrived in her love life when she started dating earnest crooner Josh Groban. While on "The Ellen DeGeneres Show," the actor revealed that her "2 Broke Girls" co-star Beth Behrs had introduced the couple to one another on account of them both being "nerds." The star gushed that she'd previously enjoyed his online repartee prior to meeting him IRL, "he's very witty on the Twitter," she smirked, which is sometimes all it takes, honestly. 

Outlets such as Pop Babble and Perez Hilton affectionately noted the twosome were an "odd couple" with the former describing them as being "a strange combination of pale mixed with nerdiness." A situation in all likelihood not helped by Dennings' supreme insistence to really up her goth game to such proportions that would make Morticia Addams look practically tanned by comparison.

During their two-year romance, the Hollywood outsider appeared to have a lot of fun playing around with morbid costuming like floor length dusty net gowns and structured dresses which jutted aggressively like bat wings at the neckline. Groban, good boy that he is, didn't choose to complement her style and instead stayed true to his sound with a bottomless closet of very nice, inoffensive suits. Hey, when it works, it works. 

A relationship breakup and a TV show breakup for Kat Dennings

By 2016, Kat Dennings and Josh Groban had split in what a source described to E! News as being "a mutual breakup" and that the two remained friends. A year later and Dennings would experience a second major life change when "2 Broke Girls" was cancelled after six seasons (via Deadline). On Twitter, the actor shared the devastating news in an aptly shared statement written with her friend and co-star Beth Behrs.

As well as thanking fans for "watching and enjoying" the show, the statement ends on the sweet note of appreciating "all the things this experience has given us," with them writing, "the most treasured is our lifelong friendship." Understandably, Dennings' sense of style looked a little limp during this time, with her usual flair and swagger absent from her red carpet looks — but she'd soon rediscover it. 

Amidst so much upheaval, Dennings did what so many of us have during times of intense change: She got bangs. Speaking to Yahoo! News, she explained her new cut had been coming "for like a decade" and how it changed her mindset. "I feel slightly perkier," she said, "like it gave me a new lease on life" — her playful Instagram selfie celebrating her new look proved as much. Clearly, some changes could be positive, and as she joined the voice cast of irreverent Netflix comedy "Big Mouth," she'd find even more positive career changes were coming.

Kat Dennings is back and more in tune with herself than ever

After a couple of years of slow and steady work which included the first season of animated sci-fi comedy "Dallas & Robo" — in which she voiced a space trucker alongside a yee-haw robot voiced by John Cena — and the wry hospitality TV movie "How May We Hate You?," Kat Dennings got her groove back, and it showed. Sartorially, the star returned to the assured slick of her resolute red lip and threw herself into structured pencil dresses which screamed power. This was a woman who knew what she was about and was ready to take exactly what she was worth. 

In 2019, she'd do exactly that by starring in — and being an executive producer of — the feminist Hulu series "Dollface" which offered a sharp comedic exploration of post-breakup female friendship and self-discovery. As Dennings told InStyle, the project was initially alluring to her because, like main character Jules, she has likewise "lost" herself "in a relationship, more than once."

"That has been my pattern, to fall for someone and then I am just gone from the world," she said in InStyle. "It's just a natural thing to do when you fall in love." Within just a couple of years, Dennings was about to "fall off the world" once again for a new man in her life, but in the most beautiful way possible. And this time, it'd be super serious super fast. 

A new phase for Kat Dennings

At the beginning of 2021, Kat Dennings would connect with Andrew W.K. and the two would quickly fall in love. As outlined by Vanity Fair, the actor may have "made her interest in W.K. crystal clear" as early as 2014 when she replied to a photo he posted on Twitter by purring, "You are a tall drink of milk AWK." As reported by Page Six, the two made their relationship official in May via some adorable Instagram posts. A few weeks later and the adorable couple had announced their engagement on Instagram, where selfies of the two acting smoochy and thirsty towards one another (and baking cookies together) had become regular components of their feeds. 

The happiness has radiated off Dennings, whose look became simultaneously more understated than ever — with the star opting for big hair and nude or pink lips — and also just as weird and witty as ever. The actor's look and spirit matches that of the similarly big haired, witty, and alternative theatrics of W.K.

Professionally, Dennings was also on a high, having returned to her role as Darcy Lewis in the hit Marvel TV show "WandaVision." As noted by ScreenRant, fans even pushed for a spinoff featuring Darcy and Randall Park's Jimmy Woo. Chatting with Entertainment Weekly, Dennings said she was also looking "to start focusing more on writing and developing and hopefully starting to direct" in her future. And by all accounts, that future looks bright.