Hollywood ‘Inception’ Rankings: Actors (Playing Characters) Playing Actors

Jordan A. Kirsch
9 min readFeb 5, 2021


Maybe it was a dream within a dream, or perhaps a movie within a movie. It could have been the fortune inside the cookie, or even the chicken, inside the duck, inside the turkey. Regardless of what shape or form the Russian doll-like event took for you personally, your first time realizing the potential complexities of seemingly ordinary experiences was likely a sensation you can’t help but remember. Reflecting on these instances in my own life (for no particular reason at all), I started thinking about how these layers have manifested in television; specifically, when TV actors portray characters who themselves are actors. Is a turducken a wild and unexpected experience? Absolutely. For me though, I’d gladly pass on the three-in-one bird-eating extravaganza in favor of watching Catherine O’Hara playing Moira Rose in Schitt’s Creek playing Dr. Clara Mandrake in The Crows Have Eyes III: The Crowening.

Whether this will better inform a future Emmy’s category or simply serve as a Month 11 pandemic respite for tired eyes, here is my Top-10 list of TV actors (playing characters) playing actors.

10. Matt LeBlanc (Joey Tribbiani): Friends

LeBlanc’s Joey Tribbiani is one of the most identifiable television characters of the past 30 years, his “how you doin?” slogan as iconic as any. A struggling actor on the show, Tribbiani’s most prominent acting role came as Dr. Drake Ramoray on Days of Our Lives. Did Tribbiani, a dumb, sleazy, sex-crazed version of perceived 90’s masculinity (overt homophobia and all), play a convincing soap-opera doctor? He did not: The mere sight of him donning a medical coat set the field back decades.

LeBlanc has shown the capacity to be a likable actor with the right role and suitable writing (check out the British comedy Episodes if you haven’t seen it), but his role as Joey and Tribbiani’s role as Ramoray don’t tell that story.

Acting Grades

LeBlanc as Tribbiani: C-

Tribbiani as Dr. Drake Ramoray: D

9. Adrian Grenier (Vincent Chase): Entourage

Time has not treated Entourage kindly.

The endearing parts, like Johnny Drama’s insanity and his relationship with Turtle, have stood the test of time. What’s (rightly) received more scrutiny as we’ve gotten further from the show’s airing, though, is how clearly it was tailor-made for a late teen, young adult, and a primarily male audience looking to have their most basic aspirations (models, mansions, Mercedes’) depicted on the small screen.

If you had to choose one character on the show who embodies these music video-like aspects of the series, it would undoubtedly be Adrian Grenier’s Vincent Chase. Chase confoundingly alternates between being carefree and neurotic, his character rarely capable of eliciting a laugh or any genuine emotion. On the occasions we see Chase acting, whether in clips from Aquaman, Queen’s Boulevard, or Medellin, those same traits hover too closely to ever believe he’s the artsy, work-focused actor we’re made to believe he is.

Acting Grades

Grenier as Vincent Chase: C+

Vincent Chase as Various Roles: C-

8. Aziz Ansari (Dev Shah): Master of None

The truth is that Ansari’s acting in Master of None isn’t what keeps you coming back to the show. Instead, it’s the writing from Ansari, Lena Waithe, and co-creator Alan Yang that does the bulk of the heavy lifting, (in addition to the brilliance of Eric Wareheim). Even Ansari’s real-life, non-actor parents are hilarious and authentic characters given the strength of the scripts and storylines, so despite Ansari’s likeability on the show, I think it’s fair to say this isn’t some sort of acting master class.

Looking beyond his job on the show as the host of Cupcake Wars, the examples we have of Ansari’s Dev Shah acting are typically in auditions. They’re…not good. Primarily a commercial actor, the show makes clear this career path is one Shah stumbled into rather than any sort of lifelong dream. What does work for Shah’s acting is the same formula to success Ansari has followed in real life; just read the lines and let that crazy little voice work its magic.

Acting Grades

Aziz Ansari as Dev Shah: B-

Dev Shah as Various Roles: C-

7. Meredith Hagner (Portia Davenport): Search Party

Hagner’s role as Portia Davenport on Search Party provides much needed comedic relief to one of the darkest comedies on TV today. For a series often busy examining the nuances and ramifications of psychopathy, Hagner’s Davenport manages to portray the dramatic effects the show’s central events have on its key characters while remaining hilarious (particularly in combination with fellow castmate John Early).

Bubbly and flighty when we first meet her, Davenport’s acting shows the progression her character goes through as she evolves from a happy-go-lucky actress willing to take any direction to a more self-possessed (albeit still flighty) performer starring as her best friend in the scripted story of one of her most harrowing life experiences.

Acting Grades

Hagner as Portia Davenport: B+

Portia Davenport as Various Roles: B-

6. Bill Hader (Barry Berkman): Barry

Seeing the actor who played Stefon on Saturday Night Live convincingly depict PTSD flashbacks to his time at war will never stop being surreal. Bill Hader’s role in both the creation and writing of Barry is one of his most notable professional accomplishments, and his portrayal of Barry Berkman in the series is similarly fantastic.

As we see Berkman attempt to make the evolution from soldier to hitman, and then to stage actor, the early bumps in the proverbial acting road are predictably constant. However, once the titular character understands the power of utilizing his past traumas to further his acted characters (with the help of the wonderful Henry Winkler), that’s when we start to see that the barriers to Berkman’s new career (there’s a lot!), may not include his acting ability after all.

Acting Grades

Bill Hader as Barry Berkman: B+

Barry Berkman as Various Roles: B

5. David Cross (Tobias Fünke): Arrested Development

We should start by acknowledging that David Cross’ Tobias Fünke in Arrested Development is one of the most criminally underrated sitcom characters of all time. Like most of the show’s stars, his lack of any semblance of self-awareness leads to his best moments. What sets him apart, though, is how untethered to reality he is compared to even his most deranged on-screen family members.

As an actor, Fünke is a disaster. Whether getting stuck in jail during preparation for his role as a prisoner or continuing to attend a methadone clinic believing it’s home to a ‘Method One’ class for method acting, no one has ever been worse at something they’ve cared so much about.

Acting Grades

David Cross as Tobias Fünke: A+

Tobias Fünke as Various Roles: F

4. Titus Burgess (Tituss Andromedon): Unbreakable Kimmy Schmidt

One of the first hit comedies to emerge from Netflix’s vault of original shows, Tituss Burgess’ role on Unbreakable Kimmy Schmidt as Tituss Andromedon catapulted the show, as well as the actor to stardom. Becoming such a part of our culture, it’s easy to forget that Andromedon’s viral Pinot Noir music video’s title was actually ‘Peeno Noir: An Ode to Black Penis.’

Andromedon hadn’t had much acting luck when we were first introduced to him. He had unsuccessfully auditioned for the Lion King on Broadway about ten times, and when he attempted to make his own version of the Disney hit, he was promptly sued for copyright infringement. His luck begins to turn as the seasons progress, however, and he’s eventually forced to choose between his acting and personal dreams.

Acting Grades

Tituss Burgess as Tituss Andromedon: A

Tituss Andromedon as Various Roles: C-

3. Sean Hayes (Jack McFarland): Will & Grace

On top of the trailblazing nature of Sean Hayes’ Jack McFarland, his character on Will & Grace was a consistent joy. His blend of physical comedy with an almost Tourettes-like delivery created a persona that, upon the show’s recent reboot, even Hayes would briefly struggle to re-inhabit.

After stints as a backup dancer, waiter, acting coach, and just about every other job you could imagine, the show’s initial run ends with McFarland finally landing a leading role as, true to character, a tough, no-nonsense, straight detective in a crime-drama.

Acting Grades

Sean Hayes as Jack McFarland: A

Jack McFarland as Various Roles: C

2. Catherine O’Hara (Moira Rose): Schitt’s Creek

Comedy is subjective and I wouldn’t be shocked to hear Schitt’s Creek isn’t atop everyone’s list of favorite shows, but if you can watch the series without falling in love with Catherine O’Hara as Moira Rose then you need to have your pulse checked. Whether through her regionless accents or ludicrous stories, O’Hara somehow manages to make a snobbish (former) multi-millionaire authentic and lovable.

When it comes to Rose’s acting, you certainly can’t accuse her of holding back. The former soap opera star’s misplaced confidence paired with a blinding desire for fame ultimately led to her role as Dr. Clara Mandrake in The Crows Have Eyes III: The Crowening. Fully committed to even the most absurd of roles, Rose’s insistence on taking this job seriously somehow forces the audience to do the same with her part in this ridiculous movie.

Acting Grades

Catherine O’Hara as Moira Rose: A+

Moira Rose as Dr. Clara Mandrake: B-

1. Tracy Morgan (Tracy Jordan) & Jane Krakowski (Jenna Maroney): 30 Rock

Is it cheating to have two characters share the top spot? Maybe. It’s my list though, and seriously, how are you supposed to rank one of these characters higher than the other? On 30 Rock, Tracy Morgan as Tracy Jordan and Jane Krakowski as Jenna Maroney embrace their out-of-touch, self-obsessed identities with reckless abandon. On the few occasions where their humanity is shown and you begin to see a glimmer of character development, they simply refuse to allow that moment to pass without reminding you just how uninterested they are in evolving.

For Jordan and Maroney, their acting on TGS and other projects are always perfect. Are they good actors? Not in any sense of the term. Would you watch their self-deluded characters vie for every possible second of screen time for as many hours as they’d allow you? Of course you would. I like to call it the Pauly Shore effect: When an actor is so clearly unconcerned by their performance so long as they’re on the screen, the result is almost always inexplicably compelling.

Acting Grades

Tracy Morgan as Tracy Jordan: A+

Tracy Jordan as Various Roles: A+

Jane Krakowski as Jenna Maroney: A+

Jenna Maroney as Various Roles: A+



Jordan A. Kirsch

NYC by way of PDX — Writing about TV, culture, and sports.