Colleen Boyle Looks Back At Her Classic "Late Night" Surprise | Letterman

She's a genuinely nice woman

Omg she's beautiful!

How am I just now seeing this? Colleen brightened my day!

My question, Colleen, is do you still laugh that way? And if so, can you please stop? 🤣🤣🤣

What a fond memory for every Dave Letterman fan. And a great piece of American television history.

She was adorable then and she's adorable now!

Yeah we were in your room see that guy right there he was sitting on your sheets "change your sheets" lol

You leave her BE! Colleen and her laugh are the BEST! ;) This is very cool and really sweet :)

NEVER forgot her. They showed it on the 5th anniversary show too.

Omg she's cute!!

This was why Letterman was great.

She is so charismatic and beautiful. Then and now. What a cool chick. A woman following letterman writers is a woman I admire deeply. So cool. I feel like I grew up partially with her because I saw this then and now I'm seeing this, it's crazy. Her accent/voice is so sophisticated but unpretentious. I'd watch a show with her now, these days. She's so charming. She should have been even more of a regular, for sure.

Classic Letterman....the early shows were hilarious. She was such a good sport. Her job at Sears really took me back to the 80's when working retail was fun.

I disagree with Colleen, you did great and looked adorable!

OMG Colleen. You were so fun and just stinkin adoreable

Well Dave did get rid of those sneakers and wear penny loafers as she suggested way back then.

I love that laugh... so cute

This is great! I can't believe they went back and found Colleen Boyle. Glad to see she's doing so well. I also grew up on LI, New York.

I thought I detected a Long Island accent on her back in the 1980s but she doesn't seem to have it anymore. Maybe she got smart, like me, and moved off of Long Island? Also, I think it's great that her friend used to tease her by leaving the words, "penny loafers", on her answering machine back in the day.

Dave was the best!

Oh man I remember that episode.

Omg she had the Annabelle doll in her room and a cross right next to it. 😂

I used to love stuff like this and Dave was so good at it. Colleen is a doll. :)

"Late Night" was such a magical show ... though really any Letterman is welcome. Love finding all of this on YouTube.

How cool!

Pardon my saying but Colleen has aged like fine wine.

Dave out & about meeting regular people was always Comedy Gold. I remember that episode well 🥰

She was still chewing gum when she went to the show. Colleen.....

What a great video segment. Really captured that moment of time. Glad folks can still laugh at each other without getting feelings hurt or taking it personal.

Dave's look at 3:15. 😂

I loved that segment back then and I love seeing it again now, October 2025. The sound-guy sitting on your bed was one of the funniest shots in television history.
Thanks Colleen for your fun personality and beautiful smile.

God I miss Letterman so much!!! There will never be another. What a tremendous human being!❤

What’s Sears?

This and "they pelted us with rocks and garbage" were my favorite Letterman moments.

The shot of the shlubby guy sitting on her bed is one of the funniest bits I'll ever see lol.

I remember I went to a Japanese Restaurant in East Northport a few days afterwards and some of the people in that restaurant was talking about that viewer mail segment with Colleen Boyle.

This was just too cool. I miss SO MUCH when late night was actually funny with hosts like Carson, Leno, and Letterman. Anymore the late night shows are like SNL ... has to use APPLAUSE signs with electrified seating to make the audience laugh on cue

I wrote a couple of letters to David Letterman. The first was when he was on NBC and it was a mock threatening letter demanding that he either reads the letter on the air or I was going to "force" him to read a Christmas song parody I wrote. It was strictly as a joke and should've never been interpreted any other way.

Well, I never saw that letter, and CBS got him. So at some point I wrote another letter reminding him of my demands. Unfortunately, at the time I was expecting this letter to be read, however unrealistic my expectations were, I dozed off through the broadcast, and woke up just as this "Letters to Letterman" segment was ending.

That was when Letterman was funny. Classic. I remember watching that episode and laughing my ass off.

Pretty sure all of us had a massive crush on her

My hardest laugh was Dave showing Colleen the crew member sitting on her bed.

I had not seen that when originally aired, but very funny and she is a cutie. Very funny.

Super cute! What a great segment!

Wait. That's the same person??

You’re a sweetheart Colleen you are still as gorgeous as ever too!!!

For all her brother knew that could have been a T-800. He could have gotten Colleen Boyle k*lled!