The Tonight Show Starring Jimmy Fallon

Detroit Special: Keegan-Michael Key, Cade Cunningham | Aired September 16, 2025

Episode Overview

Jimmy Fallon brings The Tonight Show to Detroit’s iconic Opera House for a special celebration of the city’s unique culture, sports fandom, and community spirit. This episode features Detroit native and comedian Keegan-Michael Key and Pistons star Cade Cunningham. The show is packed with humor, Detroit pride, local flavor, and memorable moments, capped off by a visit from Detroit Lions defensive end Aidan Hutchinson after a big win.

Key Discussion Points and Highlights

Opening Segment: Detroit Pride and Musical Celebration (00:05–06:55)

• Jimmy’s Detroit Welcome:

  • Opens with an energized shout of “What up, doe?” to the Detroit crowd.
  • Repeatedly celebrates the Detroit audience and city atmosphere:

    "We are in Detroit and coming to you from the Detroit Opera House." (00:05)

  • Playful banter and musical improvisation about Detroit with Keegan-Michael Key, including joking about nicknames and local quirks.

• Original Detroit Song Parody:

  • Jimmy and Keegan debut a fun, freestyle song about Detroit referencing local sports, bars, and even aspirations of “invading Canada.”
  • Keegan jokes:

    “This must be how Eminem felt when he found a word that rhymed with orange.” (05:10)

• Detroit’s Identity:

  • Jokes about Detroit having the best city nicknames and playfully cautions:

    “Be careful when you Google that last one, okay?” (referring to “the D”) (05:41)

  • Keegan riffs: “Detroit is actually a French word meaning suck at Chicago.” (05:45)

Guest Interview: Keegan-Michael Key (06:55–17:59)

• Returning Home:

  • Emotional and comedic reflections on growing up in Detroit.

    “The first thing I have to say to you as a Detroiter, because this is how we greet everyone that comes to our town, is we say, what up, doe?” (07:45)

  • Enthusiasm over being back: “It’s magical.”

• Sports Fandom and Achievements:

  • Celebrates Lions and Tigers, referencing recent Lions victory (“They won.” 08:20) and tossing the Tigers’ first pitch as a nerve-wracking experience:

    “It is way further than you think it is.” (10:01)

  • Discusses new role as co-owner of the New York Golf Club in the TGL Golf League, along with Jimmy:

    “We are limited partners in the New York Golf Club, which is one of the teams in the new TGL Golf League.” (10:47)

  • Anticipation for rematching Atlanta Drive and excitement over the indoor golf league launch.

• Comedy Roots and Detroit Institutions:

  • Keegan credits Detroit for his sketch comedy beginnings, mentioning Second City Detroit, University of Detroit Mercy, Wayne State University, and the Planet Ant theater:

    “So my theater roots, they begin right here. So much to thank Detroit for, for my career.” (13:04)

  • Humorous aside about Detroit karaoke and Motown’s legacy.

• Detroit Street Name Challenge:

  • Keegan quizzes Jimmy on the pronunciation of notoriously tricky Detroit street names such as Livernois, Dequindre, and Gratiot.
    • (“Livernois.” “Dequinder.” “Grashit.” Crowd erupts with laughter. 14:33–17:05)
    • Keegan muses:

      “There has never been a child in our city who I think should have been named Dequindre, which would have been a great name.” (15:33)

• Detroit Food Tour:

  • Shoutouts to local restaurants (SheWolf, Buddy’s, Miller Inn, London Chop House) and celebrates Slow’s Barbecue’s 20th anniversary on air, complete with rib, brisket, and cornbread tasting.

    “Cheers to Detroit. Welcome to the D.” (17:54)

Guest Interview: Cade Cunningham (18:45–23:42)

• Detroit Sports and Fans:

  • Cade celebrates Detroit fans as especially passionate and stylish:

    “This is like the most passionate city I think you could find sportswise. For sure, for sure, for sure.” (19:07) “They dress well. Everyone looks good out there. I see that.” (19:34–19:43)

• Draft Day and Roots:

  • Reflects on emotion of being drafted by the Pistons:

    “I was so happy, man… I just wanted to be part of that, you know?” (20:13)

  • Shares childhood ambitions revealed in his yearbooks (“millionaire,” then “billionaire,” then “NBA player”), leading to the panel joking about dreaming bigger every year.

• Career and NBA Changes:

  • Optimism about Pistons improvement, crediting new leadership:

    “They came in, they brought structure to us and just another hunger that really, I think helped guide us. We had a horrible year the year before they got here.” (23:07)

  • Discusses making the playoffs for the first time since 2019 (23:34).

Special Appearance: Aidan Hutchinson & Ford Field Surprise (24:12–25:15)

• Lions Victory and Onstage Recognition:
  • Defensive end Aidan Hutchinson surprises the crowd fresh from the win over the Chicago Bears at Ford Field.
  • Keegan hails Jimmy as a “good luck charm”:

    “You were our good luck Tron today. I promise you, you were. So because of that, you get the honorary game ball, brother.” (25:02)

Notable Quotes & Memorable Moments

• Keegan-Michael Key on Detroit:

  • “This is how we greet everyone that comes to our town: what up, doe?” (07:45)

• On being back home:

  • “Fantastic memories come flooding in. Everything. It’s wonderful. I just thought I grew up here and it’s just. It’s magical.” (08:00)

• On Detroit fans:

  • Cade Cunningham: “This is like the most passionate city I think you could find sportswise. For sure, for sure, for sure.” (19:07)

• Playful City Jokes:

  • “Detroit is actually a French word meaning suck at Chicago.” (05:45)

• Teamwork Acknowledged:

  • Keegan: “Who would ever think? …We’re partners forever.” (11:10)

• On food and hospitality:

  • “Cheers to Detroit. Welcome to the D.” (17:54)

Timestamps for Key Segments

• Show Intro & Detroit Song – 00:05–04:56
• Keegan-Michael Key’s Interview & Detroit Pride – 06:55–13:16
• Detroit Street Name Challenge – 13:35–17:05
• Detroit Food Sampling – 17:15–17:59
• Cade Cunningham Interview – 18:45–23:42
• Aidan Hutchinson & Lions Victory Segment – 24:12–25:15

Tone and Style

The episode is lively, cheery, and full of Detroit pride—both reverent and irreverent, mixing affectionate jokes with heartfelt appreciation. It balances playful ribbing (about other cities, street names, and sports misadventures) with genuine gratitude toward Detroit’s culture and community.

Closing

The show wraps with Jimmy, Keegan, and guests shouting out Detroit and promising to return. The entire episode highlights Detroit’s energy, humor, food, legacy, and unforgettable sports culture, providing a warm and hilarious showcase for the city.

“We had such a great time here in Detroit. Everyone’s been so nice… We love you. We can’t wait to come back.” (25:39)