Bildungsbonus Blitz: When Matthew (Never) Met Maddie
Yes, you all have to suffer that pun with me
I. Origins
Sometime after November 2008 and before January 2009
I am a senior in high school. Three things about me are pretty cringe: I am a baby liberal who is happy that Barack Obama is about to become the president. I am obsessed with the Scream franchise, to the point of writing fanfic about it. And I am a Girl Who Sings in Choir.
These disparate facets of my personality are all about to collide when my high school choir is invited to sing at the Illinois State Society Inaugural Gala.
January 19, 2009
My experience on this night is only documented by a handful of pictures. I scoured my Facebook and my LiveJournal to see if I wrote about it at all and came up empty. But the legend of this night lives on, as an oral tradition passed down from one Maddie to any soul brave enough to hear the tale.
This is not my high school choir, but this paints an approximate picture of where my choir was at the beginning of the evening. The caption on this video reads: “Pep band playing for people waiting in the coat check line at the Illinois State Society Ball in Washington, DC.” I can’t remember if we were also stationed near a coat check line, but I do remember that I left my coat somewhere in an unofficial green room area. This is important.
At some point we are released to roam the hotel for hor d'oeuvres and a possible sighting of Barry himself. While he never makes an appearance, I become awestruck by a man who I swear is Matthew Lillard, star of Scream and Scooby-Doo.
I obsess about this all night with my best friend, who tries to convince me to ask this stranger if he is who I think he is. I am not at all willing to do this, and so finally my best friend does it for me.
Best Friend: Excuse me, are you Matthew Lillard?
Not!Matthew Lillard: I don’t know who that is.
Best Friend: Oh okay, nevermind.1
I sort of think that settles it, but my best friend, who is always one to fan the flames of my delusions, objects: “Doesn’t that sound like something he would say?”
The night winds down and it is time to go home on the overcrowded DC Metro. I return to the unofficial green room area from earlier in the night to grab my coat…and it is not there. My parents and other chaperones spend some time trying to help me find it, but it is gone. My best friend then says the most cursed sentence ever uttered: “Matthew Lillard stole your coat.”2
August 31, 2021
Present-day Maddie is doing research to see if she can once and for all disprove that Matthew Lillard was ever there that fateful night. This is mostly unnecessary, since comparing the above photo to one of Matthew Lillard from the exact same month pretty much disproves my teenage delusions.

However, my research has turned up a couple of interesting tidbits from a Washingtonian write-up about the event. First:
I can confirm that Bill Murray was there (I have an equally bad picture of him), but the part I want to draw attention to is “actor Keith David, who starred in a film about a barbershop in Chicago’s south side.” If starring in a film set in Chicago was the criteria for getting invited to this event, then Matthew Lillard could have warranted an invite: he starred in the 2004 film Wicker Park, named after a tony Chicago neighborhood.
Second:
I’m 99% sure I did not leave my coat in an official coat-check room, but conditions sounded chaotic enough for coat-havers that I now feel a little bit better about losing mine.
II. Rankings
I have not seen every movie or television show that Matthew Lillard has appeared in, so please do not consider this a definitive ranking. I’m also not ranking solely on performance or solely on overall product—it’ll be a magical cocktail of both. I’ll try to touch on a little of each, and weave in the reasons I love Matthew Lillard.
7. Law & Order SVU; Episode, “Ballerina”
I don’t remember a lot about the details of this episode, but I think this is actually a very good performance from Matthew Lillard! The reason it is ranked so low is a) I’m trying to get over any malingering copaganda from my adolescent intake of all three Law & Order franchises and b) he’ll somewhat perfect this type of character in Twin Peaks: The Return. That type being a seemingly mild/bland guy with an obsession that haunts him. Arguably, this is also a more sensitive version of his performance as Stu Macher in Scream. I watched this live, and I remember being so happy to see him (even though he had stolen my coat a couple months earlier), but he was also somewhat overshadowed by Carol Burnett, the real Guest Star of the Week.
6. Without A Paddle
I 100% saw this movie in theaters and 90% thought it was good. I have not rewatched it since the year 2004 and I cannot imagine that it holds up that well. It’s a movie about three goofy bros getting lost in the woods and having to share a tent—there are definitely no homo jokes in there. I also think it reveals Matthew Lillard’s limitations as a leading man. His weirdness is what works about him, and in this movie, he’s kind of the straight man to Seth Green and Dax Shepard. If you’ve got Seth Green in full quirky mode and Dax Shepard in full Punk’d mode, you kind of need to be the straight man.
5. The Descendants
This was technically something of a comeback role for Matthew Lillard, and one that has set the template for his career right now (not counting his Scooby-Doo work). That template is: Matthew Lillard shows up in a very small/understated performance and takes you by surprise. The Descendants is a perfectly okay movie, in my opinion. And like many perfectly okay movies, it won an Oscar. I remember seeing this movie in theaters, and not knowing that Matthew Lillard was going to be the guy cucking George Clooney. Truly the highlight! Also: there will be more of this in the link round-up, but Matthew Lillard has done a lot of interviews around getting cast in this film that shed a lot of light on what it’s like to be a working actor in Hollywood who is not a big star (i.e., George Clooney). This endeared me to him even more.
4. SLC Punk!
Now this is an example of Matthew Lillard, leading man, done well. He is the central protagonist and narrator, Stevo, a twenty-something in the punk subculture in Salt Lake City, Utah. Coming of age story? Check! A cast of likeable white guys from the late 1990s? Check! A great soundtrack? Check! Minor spoilers for the movie, but Stevo’s transformation into a normie by the final frame predicts Matthew Lillard’s post-The Descendants career arc.
3. Twin Peaks: The Return; 5 Episodes
Matthew Lillard was up against more than a few obstacles when he took on the role of Bill Hastings in third season of Twin Peaks. He joined the cast of a beloved franchise (read more about my general thoughts on the franchise here), in a storyline that was initially disconnected from any of the original characters. And on top of all that, he had not watched the original show and was utterly clueless about the extra-dimensional shenanigans that his character did know about. But I think he pulled it off! He’s a normie who gets exposed to shit he cannot comprehend, and by trying to maintain his normie facade he comes complete unglued. It’s riveting. There are some fun interviews about this in the link roundup, so stay tuned.
2. Scream
“It’s a scream, baby!”
I almost love this movie too much to confine myself to a quick, quippy write-up about it. So, I’ll focus instead on Matthew Lillard specifically. It’s possible he’s mellowed on this point in recent years, but in the past, he’s been on record as disliking his performance as Stu Macher, particularly in the third act once he’s revealed as SPOILER one of the killers. He says it’s over-the-top, I say it’s perfectly unhinged.
1. His performance as Shaggy in the Scooby Doo franchise
In case you are not like me and constantly checking in on a children’s cartoon, did you know that Matthew Lillard has been voicing the character of Shaggy in all the Scooby-Doo cartoons since 2010? He of course previously brought the cartoon character to life in the live-action film version in 2002, and its sequel in 2004. In my head, I have a very specific alternative to the acting Oscars: awards for the best performances in not-great movies. And you better believe Matthew Lillard gets the gold in that contest!
III. Link Roundup
“Matthew Lillard Talks About the Most Powerful Being in Existence: Shaggy”, Justin Caffier writing for VICE
Episode of The Ringer podcast The Watch: “Matthew Lillard Talks About Turning His Career Around”
“Matthew Lillard interview: Scooby Doo, Scream, and Statham”, Sarah Dobbs writing for Den of Geek
“Twin Peaks’ Matthew Lillard on the Gruesome Fate of His Character: ‘He Was Doing It for the Chicks’”, Devon Ivie writing for Vulture
Best Friend, feel free to correct me on any of this stunningly accurate dialogue.
Best Friend, I am pretty sure that you are the one who said this. Please correct me if I am wrong.