Welcome to Retro Television Reviews, a feature where we review some of our favorite and least favorite shows of the past!  On Thursdays, I will be reviewing City Guys, which ran on NBC from 1997 to 2001.  The entire show is currently streaming on YouTube!

This week, Cassidy develops a crush on Chris while Jamal deals with a gambling problem!  Didn’t we already do all of this?

Episode 4.22 “Dating Games”

(Dir by Frank Bonner, originally aired on December 9th, 2000)

It’s time for the Valentine’s Day dance!  Why did the Valentine’s Day episode air in December?

Cassidy is upset because she doesn’t have a boyfriend.  Dawn asks Cassidy why she doesn’t just hook up with Chris since they do things together all the time and Chris is totally in love with her.  In fact …. hey, remember last week when everyone got drunk and Cassidy announced on national television that she liked Chris?  I guess Cassidy doesn’t because she tells Dawn that she and Chris are just good friends.  “I need a boyfriend!” Cassidy announces.  Dawn tells Cassidy that she’s too much into image and what other people will think.  Cassidy doesn’t hear her because she’s too busy checking out Jordan, the hottest guy at the school.  Dawn says that Jordan only dates girls who are on the rebound so Cassidy decides that she needs to pretend to date someone and fake break up with them so that she can go out with the guy she really likes.

Paging Chris!

After pretending to date Chris and then staging their breakup, Cassidy hooks up with Jordan and Chris hooks up with a girl named Linda.  However, Cassidy realizes that she actually likes Chris more than Jordan so she breaks up with Jordan.  At the dance, Dawn tells Chris that Cassidy likes him so Chris heads over to Cassidy’s penthouse and finally — FINALLY! — the two of them declare their love for each other.  Awwwwww!

Despite a silly B-plot involving Ms. Noble teaching a meditation class and an A-plot that involved everyone being kind of stupid, this was actually a pretty good episode by City Guys standards.  Maybe I’m just a sucker for romance.  Chris and Cassidy are a cute couple.

Episode 4.23 “Wager Money Go”

(Dir by Frank Bonner, originally aired on December 9th, 2000)

“Yo, Jamal,” Al says, “this gambling is making you whack!”

And indeed it is!  Jamal has developed a gambling problem.  He’s spending all of his time at a “backroom gambling joint,” where he plays craps while a local gangster watches.  Jamal swears to everyone that he has a system and he can’t lose.  However, he spends almost the entire episode losing.  It’s amazing that Jamal got addicted that quickly without actually being any good at the thing to which he got addicted.  After his friends get tired of him borrowing money from them, he steals it from the register at work.  Unfortunately, L-Train has just started working at the diner and he gets blamed for the missing money.  L-Train is out of a job and Jamal loses all of his friends.  Fortunately, Jamal comes clean, learns an important lesson, and that’s that.

While this is going on, Cassidy and Dawn make a documentary about Ms. Noble.  It turns out that Ms. Noble is kind of boring so Dawn and Cassidy try to create a crisis so they can get Ms. Noble doing something exciting on film.  There is a funny moment in which Ms. Noble refers to her husband as being “Bobby” before quickly correcting herself as saying, “I mean, Billy.”  I’m going to guess this was unscripted.  By the time this episode was shot, not even the cast could be bothered to remember the name of Ms. Noble’s husband.  Otherwise, this was yet another B-plot that revolved around how creepily obsesses all of the students were with Ms. Noble.

This was another one of those episodes where a well-established character, Jamail in this case, was required to start acting in a way that was totally out-of-character just so an important lesson could be learned.  It wasn’t terrible but it wasn’t particularly memorable either.  Do gambling joints, even illegal ones, regularly allow high school students in to play craps?  That would seem like more trouble than its worth.