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In The Office S07E11, "Classy Christmas", Darryl says:

My little girl Jada? It's my turn to have her for Christmas this year. Two years ago I had her, and we had the best time. I TiVoed her favorite shows, some things I've never heard of. iCarly You know who's funny on that show? The friend with the video camera. He's got a nice way of talking.

I don't get this joke. Does Craig Robinson have a connection to iCarly?

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    Wow, thank you for asking this question. Every time I watched that scene, I would ask myself this question but take it no further. I've watched The Office way too many times, so I've ignored this question in my head for way too long.
    – JMac
    May 7, 2019 at 19:09

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As suggested in this Reddit thread, the fun part is the randomness of Darryl finding amusement in a kids show, and especially the guy behind the camera.

Additionally, here it is implied that, since Freddie (the friend with the video camera) reached puberty during the show, his voice could have been amusing to Darryl.

A little background information of the scene from a conversation with Mindy Kaling sheds a little more light on that scene:

Corrine
I have a two-part question: a) are you or one of the other writers a fan of iCarly? and b) what made you choose Freddie (the friend with the camera) as the part Darryl would enjoy the most? Loved the random humor of that!

Mindy
Thank God for the Dads on the show. I have not seen iCarly. That was a pitch of some brilliant Dad writer.
B.J. however pitched the unaired last line of that Darryl Talking Head, which got cut for time, which broke my heart. The line was supposed to go: "That kid with the video camera? He’s got a nice way of talking." (Then, dead serious) "The Suite Life I cannot do."

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    Wow, bummer that they cut the last line. I can totally see that joke playing out.
    – JMac
    May 7, 2019 at 19:10
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    That last line worked on my just in text!
    – Todd Wilcox
    May 8, 2019 at 4:34

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