The 10 cameo roles featured in The Conners season 5 were a mixed bag. It is always tricky for sitcoms to justify big-name celebrity cameos. However, it is even trickier for The Conners to pull this off since the series is ostensibly about an ordinary working-class family. As a result, The Conners (like its predecessor Roseanne), can’t get away with bringing A-listers to Lanford every other week since this would feel even more unrealistic than high-profile cameos seem on other, less grounded sitcoms.
However, The Conners season 5 did an irable job when it came to grounding the show’s plentiful cameo roles. Not only did The Conners season 5 finale not bring back a Roseanne character (even though the episode’s plot would have allowed for this), but the spinoff also didn’t feature any celebrities playing themselves. This left The Conners season 5 with more screen time for its eponymous heroes and fewer distractions from their lives. When guest stars did show up, their characters played important roles in (almost) every episode.
10 Bobo
In The Conners season 5, episode 11, “Two More Years and a Stolen Rose,” the showrunners promised that a mystery Roseanne character would reappear on the spinoff after a multi-decade absence. However, the much-hyped comeback from this minor, forgotten Roseanne figure flopped when it was revealed that the character in question was Bobo. A one-time guest star who Dan knocked out in an episode of Roseanne, Bobo wasn’t a character substantial enough to make an impression on viewers. As such, his return didn’t mean much.
9 James
While Bobo’s return proved The Conners doesn’t need Roseanne cameos, Mark’s short-lived love interest James proved that original characters could be just as dull. Despite a spirited performance from Jarod Bainbridge, Darlene’s cafeteria co-worker James was a one-note character. His instant obsession with Mark and clinginess was an obvious gag that wore thin fast. Sadly, The Conners season 5, episode 21, “Dating, Drinking, and Grifter Logic” didn’t have anywhere else to take this character.
8 Kai the Drifter
While fitfully amusing, Harris’s love interest Kai never seemed to have much potential. Introduced in The Conners season 5, episode 9, “Crumbs and Couch Surfers,” Kai was an itinerant poet who everyone but Harris knew was bad news. Harris’s slow-burn realization of this fact was painful to watch, so it was no surprise when Kai never returned later in The Conners season 5 when Harris discovered she was pregnant with his child. Like Harris’s pregnancy plot line, this romance never really took off after a promising start.
7 Jimmie Pike
While country music star Jimmie Allen’s role on The Conners did show off his acting chops, the appearance wasted his musical talents. Since rock legend Joe Walsh’s cameo as Aldo’s father Jesse included in an impromptu jam session, viewers might reasonably have hoped for the same from Allen. However, his role as Jimmie Pike was strictly business when the singer appeared in The Conners season 5, episode 7, “Take This Job and Shove It Twice.”
6 Smitty
William H Macy was inspired casting as Dan’s bitter high school rival Smitty in “Two More Years and a Stolen Rose.” The taciturn screen veteran even got a few great scenes with Dan, and it was fun to see John Goodman spar with another working-class family sitcom’s famous patriarch. However, aside from a short Shameless reunion, Smitty’s appearance was unfortunately limited thanks to the unnecessary Bobo subplot referenced above.
5 Caleb
Speaking of Shameless reunions, Neville and Louise’s troubled teen nephew Caleb was a fun character in his brief appearance in The Conners season 5, episode 4, “Parent Traps and Heart Attacks". Played by Ethan Cutkosky, Caleb was a spiky presence who got on well with Harris. However, he otherwise couldn’t find a role for himself in the titular family. While his decision to leave for the army made sense, this is one The Conners cameo viewers could do with seeing more from in future episodes.
4 Miss Glen
While Whoopi Goldberg’s stern but fair music teacher was a likable addition to the cast of the series, her role in The Conners season 5, episode 17, “The Contra Hearings and The Midnight Gambler,” was a little limited. As the strict Miss Glen, Goldberg didn’t get to show off her comedic chops much. That said, her eventual conversation with Mark was one of the best surprises of the season as Glen revealed that Mark’s ambition alone wasn’t going to guarantee him a college scholarship. As such, she remains one of the season’s stronger new additions.
3 Doris
Louise’s mother played a solid guest role in The Conners season 5, episode 10, “The Dog Days of Christmas.” The episode saw the manipulative Doris convince Louise to take her on tour with her. This story resulted in some fun scenes between Dan, Louise, and the seemingly innocent Doris. However, The Conners guest star was way too young for her role, at a mere seven years older than her screen daughter Katey Sagal.
2 Tyler
While The Conners season 6 will almost certainly bring back Sean Astin’s Tyler as Becky’s love interest, for the time being, the character is still a guest star. A FedEx pilot introduced in The Conners season 5, episode 20, “What's So Funny About Peas, Love, and Understanding?” Tyler proved a perfect match for the sardonic, unsentimental Becky. Now, The Conners season 6 just needs to bring back Astin to capitalize on their chemistry.
1 Bev
Roseanne and Jackie’s mother Bev has been around since the beginning of the long-running series, so it almost seems unfair to consider her a guest star. However, Estelle Parsons hasn’t appeared on the series in years, and her return was limited to a few episodes of The Conners season 5. Fortunately, Bev returned in the season’s strongest storyline. When The Conners season 5, episode 8, “Of Missing Minds and Missing Fries,” revealed that Bev was suffering from dementia, this allowed Jackie a chance to forgive her mother. In the process, The Conners season 5 gave its heroine her best scenes in years and the show a perfect guest star appearance.