- Acting for Two and You Look Familiar: Where to begin?
- Jason Lee plays two different characters (different names, but suspiciously similar) in Mallrats and Chasing Amy, and a third, definitely different character in Dogma. He then reprises his first two roles in Jay and Silent Bob Strike Back, his first role in Jay and Silent Bob Reboot, and plays a completely different role in Clerks II.
- Even more bizarre, Ben Affleck plays one character in Mallrats, very different ones in Chasing Amy and Dogma, and in Jay and Silent Bob Strike Back he appears as his Chasing Amy character and as himself. He only has a brief cameo in Clerks II, though he returned to reprise his Chasing Amy role in Jay and Silent Bob Reboot, and has a cameo as a different character in Clerks III.
- Matt Damon has a cameo appearance as a minor character in Chasing Amy, plays a more major character in Dogma, and appears as himself in Jay and Silent Bob Strike Back. He also reprises his Dogma role in Jay and Silent Bob Reboot.
- Brian O'Halloran plays Dante's many cousins, all with the surname Hicks, in every VA film where he's not playing Dante. In Jay and Silent Bob Reboot, he plays Dante, his cousin Grant, and Brian O'Halloran himself.
- In addition to his regular role as Randal, Jeff Anderson plays a clerk in a gun store in Dogma.
- View Askew producer Scott Mosier plays Willam Black in Clerks, Svenning's assistant Roddy in Mallrats, the "Tracer!" guy in Chasing Amy, the "Smooching Seaman" in Dogma, and the "Concerned Father" in Clerks II. He reprised his role as Willam in Jay and Silent Bob Strike Back (where he also plays a PA on the set of Good Will Hunting II) and Clerks III.
- Joey Lauren Adams plays Gwen Turner in Mallrats and Alyssa Jones in Chasing Amy, Jay and Silent Bob Strike Back, and Jay and Silent Bob Reboot.
- Ethan Suplee is Willam in Mallrats and Clerks III, a comic book fan in Chasing Amy, the voice of the Golgothan in Dogma, and one of the guys buying weed from Jay and Silent Bob at the start of Clerks II.
- Jennifer Schwalbach plays Missy in Jay and Silent Bob Strike Back, Dante's fiancee Emma in Clerks II and Clerks III, and the Mooby's manager, Ms. McKenzie (her character from Yoga Hosers), in Jay and Silent Bob Reboot.
- Rosario Dawson plays Becky Scott in Clerks II and Clerks III, and Justice's wife Reggie Faulken in Jay and Silent Bob Reboot.
- Kevin Smith eventually got in on this in Jay and Silent Bob Reboot, where he plays both Silent Bob and himself.
- Bryan Johnson, Walt Flanagan, Mike Zapcic, and Ming Chen (a.k.a. the "Comic Book Men") cameo as themselves in Jay and Silent Bob Reboot and then as friends of Dante and Randal in Clerks III. Johnson and Flanagan are also Walter and Steve-Dave in Mallrats, Dogma, and Jay and Silent Bob Strike Back.
- Ernie O'Donnell is Rick Derris in Clerks and Clerks III, and a cop in Jay and Silent Bob Strike Back. He also had a Deleted Role as a reporter in Dogma.
- Brian Quinn is a fan at Chronic-Con in Jay and Silent Bob Reboot, and one of the guys auditioning to be in Randal's movie in Clerks III.
- Kevin Smith's mom, Grace, is the "Milk Maid" in the first two Clerks movies and a Bluntman cosplayer in Jay and Silent Bob Reboot. She also cameos at Randal's movie auditions in Clerks III, though there's no indication she isn't reprising her character from the first two Clerks pictures.
- Harley Quinn Smith is Baby Silent Bob in Jay and Silent Bob Strike Back, a little girl waving to Dante in Clerks II, and Jay's daughter Milly Faulken in Jay and Silent Bob Reboot and Clerks III.
- Justin Long reprises his role as Brandon St. Randy in Jay and Silent Bob Reboot, and plays a hospital orderly in Clerks III.
- Actor-Inspired Element: Jay's many catchphrases ("Snoogins," "snoochie boochies," "snooch to the nooch") all evolved from random vocalizations Jason Mewes made for his friends that literally meant "I'm just kidding."
- Channel Hop: Quite the list. Clerks was done at Miramax, while Mallrats was done at Gramercy Pictures; Chasing Amy went back to Miramax while Dogma was done released by Lionsgate for its theatrical release and Sony Pictures Home Entertainment (then Tri Star Home Entertainment) when Disney (then owners of Miramax) objected to the films release due to controversy. Jay and Silent Bob Strike Back went back to Miramax one last time when The Weinstein Brothers left the company in 2005, releasing Clerks II with MGM due to their deal with The Weinstein Company. After the series went dormant for 12 years, following Harvey Weinstein's fall from grace, Saban Films picked up the North American theatrical rights for Jay and Silent Bob Reboot with Lionsgate doing Home Video rights due to their Home Video deal, while Universal got the rights for international distribution. With Paramount acquiring 49% of Miramax, they eventually got the rights to all the Pre-2005 View Askew films sans Mallrats (staying with Universal) and Dogma (personally owned by the Weinsteins), while Lionsgate got the rights to the Weinstein Company's library post 2005 (which includes Clerks II), on top of distributing Clerks III themselves.
- Descended Creator: Writer/director Kevin Smith plays Silent Bob (and himself in Jay and Silent Bob Reboot).
- Executive Meddling:
- Funny Character, Boring Actor: Subverted with Jason Mewes. While the character of Jay was based on things he'd do to amuse himself when he was sixteen, adult Mewes has always been extremely shy and quiet.
- Irony as She Is Cast: While Kevin Smith and Jason Mewes are almost as inseparable in real life as they are on screen, there is one difference between reality and fiction: in the movies, Jay never shuts up, while his lifelong friend Silent Bob, true to his name, almost never talks; in real life, their dynamic is the opposite, with Smith being known for being a Motor Mouth and Mewes being more reserved.
- Production Posse: The main cause of You All Look Familiar. Smith tends to work with some of the same people on the production crew and give them cameos.
- Referenced by...: Bennett the Sage referred to it a couple of times.
- Sage is called by Jay's nickname for Silent Bob, "Lunchbox".
- Speaking of Silent Bob, Bennett compared the casting of John DiMaggio as Golgo 13 in his review of the Queen Bee OVA to Gary Oldman being cast as Bob.
- Those Two Actors: Lampshaded in Jay and Silent Bob Strike Back.
- Trilogy Creep: Chasing Amy was originally supposed to be the final VA film (hence its original title, "The Jersey Trilogy"), but then Jay and Silent Bob found their way into the script for Dogma.
- Word of Gay: Kevin Smith confirms that Jay is a deeply closeted (or so he thinks) bisexual.
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