For the past eight seasons, Jake Peralta, Ray Holt, Terry Jeffords, Rosa Diaz, Amy Santiago, Charles Boyle, Hitchcock, and Scully made us laugh, dance, sing, cry, and laugh again throughout each tremendous season. However, part of the big reason that Brooklyn Nine-Nine is such a memorable show is because of the numerous guest stars that have appeared throughout the series.
The series always managed to find a hilarious way of incorporating notable names into the big world of Brooklyn Nine-Nine. Though the series ended in 2021, the impact it made has kept it relevant long in pop culture. To celebrate this amazing show, we’ll count the five best recurring guest stars in the series.
Craig Robinson (Doug Judy)
Who could forget the budding bromance between Jake Peralta and Doug Judy? The writers did an excellent job of giving Judy’s character dimension: he was charming, caring, and a criminal scumbag. Still, his personality was one of the sweetest things about the series. It helps that a veteran of Craig Robinson‘s natural charisma is the one bringing this role to life.
The ways that Doug Judy would escape each episode were quite clever. The writers knew we would be on high guard about Doug because he’s a criminal at heart. So the fact that the writers wrote the recurring gag without undermining Jake and insulting the viewers is quite impressive. It could be argued that Doug Judy is the best recurring character in the series, though he does have some tough contenders on this list.
Vanessa Bayer (Debbie Fogle)
Debbie had fewer episodes than the other names on this list, but she still made a huge impression throughout her short run. Her panicked and highly cautious character was a great juxtaposition to Holt’s character when she was introduced in Manhunter, but her integration within the team was great in the Jimmy Jab Games II.
Her solo episode, Debbie, brought nice depth to the character while playing off her strengths. Sadly, Debbie turned out to be a theft working for a high-level criminal, but the character went out with a bang as her zingers were great throughout. Her odd love for Jake and her ability to beat both him and Rosa was a standout (and hilarious) moment. Vanessa Bayer was perfect for this role as she knocked it out with ease.
Dean Winters (Keith Pembroke aka The Vulture)
Who knew Mayhem from those All-State commercials would be such a great actor? On a series note, Dean Winters has memorable roles up and down his filmography, but Brooklyn Nine-Nine re-enforced just how great of an actor he truly is. The Vulture came out swinging quickly in his debut and the montage of his character stealing criminals (or Charles’s latte) was one of the best moments of the series.
His interactions with each character were always fun. His admiration for Terry, his weird love/hate for Jake, and his banter with Charles created a different dynamic that made his interactions so witty. Admittedly, the show didn’t get as much out of The Vulture as they could when he temporarily made Captain in season three, but they still managed to take advantage of the great chemistry he has with the cast.
Kyra Sedgwick (Madeline Wutch)
Captain Holt’s one-liners were at his best whenever he saw Madeline Wutch. Their rivalry throughout the seasons was wildly entertaining and the chemistry between Sedgwick and Andre Braugher was incredible. They’re both essentially the same stoic and humorless characters but the way these two delivered their lines was top-notch. It was great that the writers gave Holt a rival as it helped bring out more dimension to his character, and despite how vengeful Madeline Wutch was, she still had a likable charm in the series.
Jason Mantzoukas (Adrian Pimento)
Pimento’s character brought most of the show’s dark humor to the series. It was a bit jarring at first to have such a tormented figure play a central role in the series, but Pimento’s antics quickly meshed well with the cast. His relationship with Rosa felt a bit forced (even though Rosa has a thing for messed up people), but it did maturely develop her character. Pimento was the complete opposite of every cop on the series and that made him stand out even more.
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