- Actor Allusion:
- In "Can't Buy Me Love," after T.J. asks him if he's seen the honest tax return that T.J. decided to submit instead of a dishonest one filled with fraudulent deductions, Coach Gerber tells T.J. that he's planning on going to Cuba to buy cheap Cuban cigars to import and resell them in the States in order to pay back the money he owes to the IRS. Before Gerber discloses his plan, T.J. asks if he's "given up on the whole law and order thing, then?" Gerber's portrayer, Dann Florek, played NYPD Captain Donald Cragen in Law & Order from 1990 until 1993, when was fired from that show as a byproduct of an order by NBC executives to add more women to the show's cast; the season after Smart Guy's cancellation, he reprised the Capt. Cragen character in Law & Order: Special Victims Unit, remaining in that role until 2014.
- During "The Soda Wars", the final scene before the episode's end credit blooper montage features Mo Tibbs (played by Omar Gooding) trying to pitch a new low-calorie soda to Colonel Bubble executives. His pitch goes well until he jumps off the table and injures himself. The CEO of the company promptly asks "does he have a brother?"
- Banned Episode: Subverted with "Strangers on the Net". Disney Channel initially excluded the episode from its rerun cycle, due to the "A" story involving T.J. and his friend Karen being contacted by a serial child predator on a chat room for kids. However, the channel reversed course on this decision due to the episode's internet safety Aesop.note
- Celebrity Star: Destiny's Child (featuring a young Beyoncé) guest stars in the aptly-titled season three episode "A Date with Destiny," offering T.J. the opportunity to be in their music video and later the chance to go on a world tour with them.
- Dawson Casting:
- Word up. Marcus (not an egregious example, considering Jason Weaver was a couple of years older than Marcus), Mo (who fits as in the first season, Omar Gooding was playing 15-year-old Mo, while in his early 20s) and Yvette (her portrayer, Essence Atkins, is actually too close in age to John Marshall Jones who plays Floyd for them to be father and daughter in Real Life; there is only a ten-year age difference between the two). It's a bit odd that Gooding and Atkins play high schoolers in the show when you consider that Gooding's character in Hangin' with Mr. Cooper (which ended a few months after Smart Guy debuted) was revealed to have graduated high school in the show's final season and Atkins played a college freshman almost four years earlier in the pilot episode of Saved by the Bell: The College Years, before her character was written out.
- This also applies to many recurring cast members, such as J.D. Walsh (Mackey), Tinsley Grimes (Nina) and Arvie Lowe, Jr. (Deion), who were also in their early 20s during their runs on the show. It's pretty peculiar when you consider that the Disney-produced series that came after the show ended had most of the teenage characters played by young actors exactly or very close to the same age of their characters.
- Handily averted with T.J., as Tahj Mowry was the same age as the character.
- Name's the Same: Reagan Gomez (then Gomez-Preston) and Tinsley Grimes play characters named Nina in different seasons (the African-American Gomez plays Nina Duperly, Marcus and T.J.'s love interest in "Love Letters;" Caucasian Grimes plays Nina [No Last Name Given], Yvette's best friend in several season three episodes).
- Prop Recycling: The pilot used the Matthews house and the John Adams High School classroom and corridor sets from Boy Meets World.
- Technology Marches On: Inverted as the technology featured in the show may be a bit ahead of its time (though not a lot of people may be aware that some of it had existed at the time of the show's run).
- In "Diary of a Mad Schoolgirl", T.J. works with another student on a project about Lizzie Borden through file sharing.
- In "Stop the Presses", T.J. deletes Marcus and himself from a family photograph (keeping a swimsuit-clad Yvette to print in T.J.'s newspaper as retaliation for stealing a story scoop) using a Photoshop-style (not long before Photoshop existed) program.
- In "That's My Momma", T.J. mentions to Floyd that one can watch SportsCenter online and make phone calls over the computer (since this was the late 1990s, streaming SportsCenter which didn't become possible until the very late 2000s through the WatchESPN streaming service or any video online would only be possible with minimal issue with broadband/high speed internet, which was only starting to be widely rolled out and was relatively expensive at the time the episode aired; making phone calls over the computer is a bit antiquated these days since one can talk to someone via a webcam videophone-style service such as Skype).
- Played straight though in "Beating is Fundamental", which has T.J.'s nemesis Blake Jordan complain that T.J.'s computer (presumably his internet connection) was slow, implying he had dial-up service.
- Unintentional Period Piece: Aside from the fashion sense of some characters (Yvette's tam hats in some earlier episodes, especially), the series made quite a few pop culture references that date the show to the late Nineties.
- You Look Familiar: Naya Rivera and Kyla Pratt both appear in "Baby, It's You, and You, and You" as two of the dates T.J. is set up with for a school dance. Rivera appears again in "Never Too Young," as Kelly (a girl T.J. accidentally tells a story told about one of the partygoers that involved her), while Pratt plays Brandi (T.J.'s streetwise friend) in "Bad Boy" and "She Got Game".
- Taraji P. Henson guest starred as Monique (one of the dancers in T.J.'s music video project) in "Big Picture," and as Leslie (one of Yvette's friends) in "Break Up Not to Make Up" and "Boomerang".
- Coby Bell (who ironically later co-starred with Tahj Mowry's sister Tia in The Game (2006)) guest stars as Garret (a guy who was interested in Yvette) in "The Dating Game" and Anthony "The Hammer" Williams (a basketball player whom T.J. tutored) that same season in "Most Hated Man on Campus".
- Bianca Lawson played Shirley in "Baby, It's You, and You and You" and Tracy, Mo's two-timer girlfriend in "It Takes Two". Coincidentally, in both episodes, her characters served as romantic interests of Mo.
- Jennifer Lyons plays Celia (a member on Yvette's cheerleading squad who is the first person T.J. meets on his first day of high school, whose character name is not said outright) in the Pilot Episode, and Lisa (who beat Yvette for the lead in a play, likely because of her new breast implants) in "From A to Double D".
Trivia / Smart Guy