David Letterman and Conan O'Brien, Part 1: 1993-2009

Don Giller
Don Giller
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Published 2018-08-28
September 13, 2018, marks Conan O'Brien's 25th year on late night television. Here's a two-part Dave/Conan compilation to commemorate the milestone.

Part 1 documents Dave's and Conan's interactions on each other's shows from 1994 to 1999, followed by Dave's reactions when Conan was awarded The Tonight Show in 2004 and then finally took over the show in 2009.

In the absence of further appearances, Part 2 is devoted mostly to Dave's gags and running commentary on the fiasco that was The Tonight Show in January 2010. The collection ends with Conan's last Late Show guest appearance in 2012.

Part 1
Beginning where we left off before Conan's Late Night debuted:
1. June 25, 1993. On the final Late Night with David Letterman, Dave wishes Conan well and hopes to someday be invited onto his upcoming show.*
2. February 28, 1994. Dave guests on Late Night with Conan O'Brien.
3. July 29, 1994. Conan guests on Late Show, 1.
4. March 21, 1995. Dave's pre-Oscar nightmare.
5. May 2, 1995. Late Show's stand-by audience is sent to LNwCO. (Inclusion of the giant rat at the beginning is paid off at the end.)
6. December 19, 1995. A Day in Dorothy's Life (excerpt).
7. January 26, 1996. Conan guests on Late Show, 2.
8. February 23, 1996. Cold Open on LNwCO.**
9. February 6, 1996. Joan Collins guests on Late Show (excerpt).
10. March 19, 1996. Dave makes a surprise appearance on LNwCO to talk to Joan Collins.***
11. March 27, 1996. Dave goes to LNwCO and gives Conan a joke.
12. May 24, 1996. Dave and Conan in Late Show's cue cards room.
13. June 24, 1996. Conan guests on Late Show, 3.
14. January 13, 1999. Conan guests on Late Show, 4.
15. October 15, 2003. Dave announces the birth of Conan's and his wife's baby, Neve.
16. September 27, 2004. Dave on Conan hosting The Tonight Show -- in five years.
17. June 1, 2009. Dave on Conan as the new Tonight Show host.

Thanks to @therealtriggi on Twitter for the idea.

*A look at the media coverage and Dave's Late Night segments in the Spring of 1993 when NBC announced Conan as the next host of Late Night after Dave would leave NBC for CBS is here:    • Conan, Jay, and Dave, April-June 1993  
**Thanks to Bill Bredice for the video.
***Video courtesy Inflatable Conan's upload here:    • David Letterman's surprise appearance...  

Part 2 here:    • David Letterman and Conan O'Brien, Pa...  
All Comments (21)
  • @jondavis2790
    You can see Conan getting more and more confident.
  • @chrisfenwick5376
    It really is amazingly nice and generous how letterman saved conan’s late night show by appearing the first time. Ratings were so bad for him those first couple months, letterman was still bitter at nbc for how he was treated. He didn’t need to do it but he loved conan so much that he went out of his way to sit down at a show that replaced him at a company that he still had hard feelings for and gave it a stamp of approval. Just an amazingly kind gesture. Letterman will always have my respect for that and he was already a legend.
  • @tommylakindasorta3068
    I really sense how relieved Dave was that his Late Night show was in good hands with Conan. Like a proud father.
  • @chrisreid7758
    Dave made the “Conan killed a guy” joke in the very first clip…and then once more in the very last clip….16 years apart. Incredible.
  • @Surreal469
    Dave's wish for Conan to end up the same as Dave was VERY prophetic
  • @240p_is_enough
    I love seeing Dave genuinely laugh at Conan's stuff. Wholesome.
  • @johnking5174
    Through all of this you can see the affection and respect David Letterman had for Conan O'Brien, and indeed vice versa.
  • @blanchardwill
    One of my favorite Giller joints. Letterman was meaningfully supportive of Conan and treated him as a peer and honorable successor on the Late Night show. It’s exactly the opposite of what Leno did, who passively demeaned Conan during his TV debut. It’s a testament to how real and passionate about broadcasting Letterman was. A lot of people were not into Conan in the 90s especially at NBC, but Letterman supported him every step of the way before Conan blew up. That’s class, man.
  • @patmccrotch7645
    There's something that makes me so happy seeing these two together talking and doing interviews with one another.
  • @Novastar6
    Conan looked defeated on that Letterman episode. Dave came in at the exact right time.
  • @Football__Junkie
    Dave was for Team Coco from the beginning. Coming on and giving a seal of approval and laughing at all of Conan’s jokes.
  • @MrNemoYo
    Dave, Conan and Craig... The trinity of late night.
  • @bijibadness
    1:50 was it, man. not even "sink or swim" for Conan O'Brien, more like "we're sinking already and we're probably going to be off the air in a few weeks. if there's a shot to survive as show and as an entertainer, it's right this second. let's start this thing." gosh, I admire Conan. because he's funny and the best, true, but look at that. if anyone doesn't know, Conan O'Brien's show was a giant flop for the first however many months. it was this episode he's said on many occasions that was the last chance. and David did this as a favor. Dave didn't really DO interviews. this was the show it very literally all turned around for Conan O'Brien. we get to watch a man's career get made after being told it wasn't going to happen. how amazing. thanks for this, Don. I've thanked you before. thanks, man.
  • @bleepiestofbloops
    Wow, seeing Conan on Letterman right after Dave was on his show really highlights how green Conan was at hosting. He seems much more like himself just a few months later, as a guest.
  • @mr.mountvillain362
    I love how Dave knew NBC screwed him over, but he knew it wasn't Conan's fault and never blamed him at all, just gave him his blessing and tried to help him as much as he could for many many years
  • @adamdesanti6713
    Two beloved men from 2 different generations. Dave's stuff from the 80's was very avant-garde and Conan in the 90's was my generation.