Kevin Smith raising eyebrows

Kevin Smith’s career has always been closely tied to his personal experiences. He first hit the pop culture scene in 1994 with "Clerks," a film inspired by his own time working behind a cash register. In 2022, he debuted "Clerks III," which follows Randal Graves (Jeff Anderson) as he makes a movie about working at Quick Stop after suffering a life-threatening heart attack. This obviously reflects Smith’s beginnings as a director, but also the heart attack he suffered in 2018.

This heartfelt approach has earned Smith a loyal fanbase that will turn out to watch pretty much anything he puts out into the world. Similarly, the beloved director has amassed a group of famous friends who love working with him so much, they readily find time to pop up in his movies. If you’re watching a Kevin Smith flick, you’re sure to encounter at least a handful of cameos. With his art reflecting his life more than ever before, there’s never been a better time to take a look at these very small roles, which are often filled by very big names. Some are significant to the story, some coast by on sheer celebrity, and some are delightfully unexpected. Each and every one is immensely fun to spot. These are the best cameos in Kevin Smith films, ranked.

13. Justin Long

Brandon St. Randy in court

Before Marvel gave us the MCU, Kevin Smith assembled his own cinematic super-story with the complex timeline of the View Askewniverse. Not every Smith movie is part of the fictional New Jersey landscape that defines the View Askew films, however. Horror films "Tusk" and "Yoga Hosers" take place in Canada, while another horror film, "Red State," is set somewhere in middle America. Moreover, "Jersey Girl" may take place in Smith’s home state, but it doesn’t feature any View Askew characters.

And then there’s the Pennsylvania-set "Zack and Miri Make a Porno." Although this 2008 flick is similar in tone to Smith’s other work, it isn’t directly connected to "Clerks" and its ilk — with one major exception. Here, Justin Long plays adult film actor Brandon St. Randy. This character pops up again in 2019’s "Jay and Silent Bob Reboot," where Brandon St. Randy is the lawyer who keeps Jay and Silent Bob out of jail for dealing drugs, while also suing them for copyright infringement on behalf of Saban Films, who recently purchased the rights to their names.

Long brings a lot of campy fun to this small cameo. The film never comes out and says his name, but everything about him confirms he’s the character from the 2008 flick. Aside from being entertaining, this cameo also makes the list for bringing "Zack and Miri Make a Porno" into the View Askewniverse.

12. Ben Affleck and Matt Damon

Ben Affleck and Matt Damon in bar

Ben Affleck first worked with Kevin Smith in 1995’s "Mallrats," in which he plays antagonist Shannon Hamilton. They reunited in 1997’s "Chasing Amy," which also brought Matt Damon into the mix. Both Affleck and Damon returned for 1999’s "Dogma," and many subsequent Smith films. They’ve worked with the director so often, it can hardly be called a "surprise" when they show up — but it’s always a delight.

2001’s "Jay and Silent Bob Strike Back" contains what might be Affleck and Damon’s best cameo. Affleck appears as Holden McNeil, his "Chasing Amy" character, to explain the internet to the titular heroes. Then he shows up as himself alongside Damon, also playing himself, when Jay and Bob wander onto the set of the fictitious "Good Will Hunting 2: Hunting Season."

The scene is hilarious. For one thing, the idea of making a mindless sequel to a prestige film like "Good Will Hunting" is funny on its own. Then there are the cameos from director Gus Van Sant (counting piles of money) and Scott William Winters (once again playing the preppy guy in the bar). But Affleck and Damon playing exaggerated versions of themselves is just great — especially because they seem to be having a ball.

11. Shannen Doherty and Wes Craven

Shannen Doherty questioning Wes Craven

"Jay and Silent Bob Strike Back" sees the titular pair stumble through multiple movie sets, including that of the latest "Scream" film. Director Wes Craven and stars Shannen Doherty and Suzanne the orangutan all appear. While the idea of a great ape playing a serial killer is funny on its own, what makes this scene so special are the connections Kevin Smith has with Craven and Doherty.

Doherty’s bond with Smith is straightforward: She’s one of the stars of "Mallrats." The Craven connection is a bit more complicated. 2000’s "Scream 3" also takes place in Hollywood, with much of the action happening during the filming of fictional horror sequel "Stab 3: Return to Woodsboro." At one point, Gale Weathers (Courteney Cox) gets escorted off set by two security guards as a bunch of tourists wander by. One of those tourists is Wes Craven, while two others are Jay and Silent Bob. Thus, Craven’s cameo in "Jay and Silent Bob Strike Back" is a particularly sweet bit of synergy.

10. Melissa Benoist and Val Kilmer

Val Kilmer and Melissa Benoist frowning

Within the View Askewniverse, the movie adaptation of "Bluntman and Chronic" is released in 2001. Almost 20 years later, Saban Films buys the rights with the intention of rebooting it as "Bluntman v Chronic" in "Jay and Silent Bob Reboot." They hire director Kevin Smith (who, yes, exists within his own fictional universe) to helm it. He casts "Supergirl" star Melissa Benoist as Jay/Chronic and former Batman Val Kilmer as Silent Bob/Bluntman.

Even if you know nothing about Kevin Smith outside of his filmography, you know he loves Batman — references to the Caped Crusader are all over his movies. He even named his daughter Harley Quinn after the infamous Gotham baddie. Thus, the fact that he actually got to put a former Batman in one of his films is incredibly rewarding. Not to mention the fact that Kilmer plays a character based on a character Smith plays himself.

9. Jason Biggs and James Van Der Beek

Jason Biggs and James Van Der Beek at Chronic-Con

In "Jay and Silent Bob Strike Back," 2000s teen stars Jason Biggs and James Van Der Beek are cast as the titular superheroes in "Bluntman and Chronic." At the time of the film’s debut, Biggs was best known for the "American Pie" films, while Van Der Beek played the eponymous Dawson on "Dawson’s Creek." Thus, when the real Jay and Bob literally crash into their dressing room, they recognize Biggs as the guy who had intimate relations with a pie and Van Der Beek as "the Dawson," as they put it.

Both actors are fantastic as self-involved and exaggerated versions of themselves, but this moment isn’t the one we want to talk about. Rather, the scene that makes this list is their very short reappearance in "Jay and Silent Bob Reboot." For one thing, it’s nice to see Smith honor his own continuity by having Biggs and Van Der Beek return to attend "Chronic-Con." Secondly, Biggs’ indignation over the fact that a "Bluntman and Chronic" movie is happening without him and that it’s going to be directed by Kevin Smith is genius. He’s utterly convincing as a bitter, jilted actor, and Van Der Beek plays off it expertly.

8. Carrie Fisher

Carrie Fisher smiling as nun

When Jay and Silent Bob discover internet trolls talking smack about them because of the upcoming "Bluntman and Chronic" movie in "Jay and Silent Bob Strike Back," they decide to travel to Hollywood to sabotage the film. However, neither one has a car. They try to take a bus, but that’s too expensive. So, they resort to hitchhiking.

A fellow hitcher played by George Carlin tells them that if they want to get a ride, they must provide sexual favors for the driver. The duo is initially shocked, but the hitcher explains that this is a simple rule of the unwritten book of the road. Jay and Bob are then picked up by a nun played by Carrie Fisher. As she’s a nun, she often refers to the Bible as "the book." Jay misinterprets this as the unwritten book of the road and attempts to fulfill his duty as a passenger.

It’s a perfectly awkward scene. The audience knows what she’s talking about, and we know what Jay thinks she’s talking about. The whole time, you’re hoping he doesn’t do what he’s going to do, but every part of your being is certain that he will, and that it won’t end well. Carrie Fisher (the first of two "Star Wars" cameos in this film) is perfect: She plays the nun with earnestly charming naivete.

7. Jason Lee

Lance Dowds sneering polo shirt

Jason Lee has appeared in so many Kevin Smith movies, it’s shocking when the director doesn’t put him in something. It isn’t exactly a surprise, then, to see him in 2006’s "Clerks II," but it’s definitely a treat to watch Lee finally interact with Dante and Randal. But that’s not why this scene makes the list.

Dante and Randal are two men in their 30s who haven’t amounted to much. They worked at Quick Stop for several years before it burned down, then, instead of letting the store’s destruction motivate them to take their lives in new directions, found work at a Mooby’s fast food joint. Lee plays Lance Dowds, a tech mogul who went to school with the clerks and shows up at Mooby’s just to ridicule them.

This is a crucial moment in Dante and Randal’s development. Lance’s words cut deep, though Randal is reluctant to admit it. He ditches the restaurant to ride go-karts and remind himself of a simpler time. At the end of the film, Randal confesses to Dante that they should buy Quick Stop and reopen it. Although he likely comes to this conclusion the minute the place burns down, one can definitely argue that Lance’s visit is what pushes him to admit the truth to Dante.

6. Chris Hemsworth

Chris Hemsworth Chronic-Con hologram

There’s no shortage of surprise cameos in "Jay and Silent Bob Reboot": Nearly every scene features a recognizable face popping in to say a few lines. Some are standard Smith collaborators, while others (like Fred Armisen and Molly Shannon) are comedic actors doing a fun bit part. But one cameo is totally unexpected.

Early on, Milly (Harley Quinn Smith) admits to having a massive crush on actor Chris Hemsworth. This isn’t a surprise — the Thor actor is a famous heartthrob — but Hemsworth’s inclusion in the film itself definitely is. When the characters arrive at Chronic-Con, a hologram of Chris Hemsworth directs people towards certain events and delivers a list of rules about how not to interact with his hologram.

Prior to this, Hemsworth had never worked with Kevin Smith. Sure, Smith is a famous fan of superheroes, but that doesn’t mean the Avengers are going to start shopping at Quick Stop. This makes Hemsworth’s appearance a total shock and an absolute delight, especially since he gets to use his serious comedic chops.

5. Mark Hamill

Supervillain Mark Hamill holding up fist

Even if you’ve only seen a single scene of one of Kevin Smith’s movies, chances are good it contained some kind of reference to "Star Wars." He’s made his love for the saga clear from the very beginning: Who can forget the moment "Clerks" stops to consider the many independent contractors killed at the end of "Return of the Jedi"?

Smith’s love of "Star Wars" comes to a head when Mark Hamill crashes through the walls of the Bluntcave in "Jay and Silent Bob Strike Back." He’s playing Bluntman’s nemesis, who sports a giant fist. It’s a delight to see the man who played Luke Skywalker devour the scenery in this campy role — he even uses a Bluntsaber.

Not only does this connect Smith to "Star Wars," it bonds him to Batman as well. Hamill is widely beloved among Bat-fans for his iconic performance as the Joker in "Batman: The Animated Series." This isn’t the last time Smith worked with an actor from that series either: In 2016’s "Yoga Hosers," Kevin Conroy, the voice of Batman, plays a customer in the Canadian convenience store Eh-2-Zed.

4. Redman and Method Man

Redman and Method Man in car

"Jay and Silent Bob Strike Back" wasn’t the only stoner comedy released in 2001. In December of that year, a film called "How High," starring rappers Redman and Method Man, hit theaters as well. Kevin Smith pays homage to them in "Jay and Silent Bob Reboot" by making his characters fans of the latter film. Then things get really meta when Jay and Silent Bob have a cannabis-induced vision of Redman and Method Man.

If you’re a fan of behind-the-scenes stuff, this moment is great. But that’s not why it’s on the list. It has a spot because it’s both important to the plot and everyone is really, really good in it. Jay and Silent Bob play off Redman and Method Man so well, it makes you want to see an entire film starring the four of them. Plus, the advice Jay gets helps propel him through the rest of the movie. This moment is both a satisfying tip of the hat to a fellow stoner duo and a piece of excellent storytelling.

3. Alanis Morissette

Alanis Morissette looking judgmental

"Dogma" is packed with controversial elements. For one thing, it posits that Jesus may have had brothers and sisters, which many Christian traditions dispute. Another example is Rufus (Chris Rock), an apostle who was left out of the Bible because he’s Black. Oh, and Jesus is Black as well. Instead of leaving Christ out of the New Testament, the powers that be simply changed his race. And then there’s God. In the View Askewniverse, God is a woman played by Alanis Morissette.

Morissette came to international fame in the 1990s for her unabashedly angry alternative rock album "Jagged Little Pill." Casting someone who sings frankly about bitterness, sexual harassment, Catholic guilt, and jealousy to play God is, to put it mildly, a gutsy choice. But of course, this is a Kevin Smith movie, where pretty much anything goes. The sheer novelty of Morissette’s appearance is delightful, and she’s utterly wonderful in the role. This God is both powerful and gentle, with a quirky playfulness that is somehow strangely comforting.

2. Will Smith

Will Smith and Ollie Trinké chatting

"Jersey Girl" isn’t one of Kevin Smith’s most beloved films. That’s not to say it’s bad, though. This 2004 flick tells a sweet story about Ollie (Ben Affleck), a single dad who must find a way forward after losing his job as a publicist. Not only is it the closest thing we’ve ever gotten to a family friendly Smith film, it’s also the first entry in his oeuvre to tackle the subject of fatherhood, something that frequently comes up in his later films.

Throughout "Jersey Girl," Ollie is desperate to leave Jersey behind and get back to his life as a Manhattan PR executive. He’s so bent on this, he’s willing to skip his daughter’s talent show for a job interview. While waiting in the lobby of the firm, he encounters Will Smith. Insulting Smith in a heated moment is what cost Ollie his career in the first place. Luckily, Smith has no idea who Ollie is. The two men sit in the lobby discussing fatherhood, and Smith admits that parents, including himself, are largely clueless. This conversation inspires Ollie to abandon the interview and rush to his daughter’s side. It’s a gorgeous scene, perfectly acted by both Smith and Affleck, and an excellent example of an "I can’t believe they got him!"-style cameo on the former’s part.

1. Stan Lee

Stan Lee in Mallrats

Before the Marvel Cinematic Universe decided to put the legendary Stan Lee in almost all of its movies, Kevin Smith showed us what the comic book legend could do on the big screen in 1995’s "Mallrats." Brodie Bruce (Jason Lee) is a devout comic book fanatic, and Stan Lee is one of his heroes. He can’t believe it when he finds out that the Marvel mastermind is doing a signing at his local mall. Brodie’s been going through a lot, so his buddy T.S. (Jeremy London) gets Lee to give Brodie some relationship advice.

Lee explains that most of the characters he created are reflections of the anguish he experienced after losing the love of his life. Moved by his idol’s words, Brodie decides to get his girlfriend back. Naturally, Lee made up the entire story to get through to Brodie, but that doesn’t make the moment any less meaningful. Lee also appears in "Yoga Hosers" and "Jay and Silent Bob Reboot," but his first appearance in a Smith film is still the best. In fact, this might just be the best Stan Lee cameo in any movie. There’s simply no more impressive role for Stan Lee to play than himself.