When you go from a hot chick to a penis in chatroulette.
"Damn it! She said she was going to show me her boobs, but then I got Dickrolled".
by Almoney50 September 6, 2010
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Similar in nature to the rickroll, dickrolling (or to dickroll someone) is when you send someone a link to chatroulette, knowing they've never been there before, only to assume the first video served up will be a nice, close shot of some dick.
"Dude, have you seen that website, chatroulette? There's so much dick on it!"

"Yes, Susan, in fact I have. My mom sent me a link to it without telling me what it was and the first thing I saw was a dick!"

"You're mom dickrolled you! She's so bitchin!"
by Mr. Dick Roll March 14, 2010
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A variation on the rickroll. Placing a link on a web page that purports to link to interesting content but is in fact a link to a video of Dick Cheney.
Some guy on reddit posted a link in a comment that was supposed to be a lolcat, but it was really a dickroll! Boring!
by AtomicLlama April 22, 2008
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When you assault a construction worker and take his steamroller, proceeding to do a girl doggystyle while singing a Third Eye Blind song and shoving wheatgrass into her anus.
Man, I was giving Casie a california dickroller; I must say sir, the shit 'twas ign'ant.
by big mac smash October 12, 2014
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The practice of trolling someone by sending someone an autoplay video of an amatuer pornographic video or image made by the targets parent(s).

Ideally set to the song "never gonna give you up" by Rick Astley, the practice is an evolution of rickrolling, one of the formative trolling practices of the late early internet .
1/ "the practice of rickrolling began in late 2022 when an urban dictionary contributor, posting under the nom de guerre

'Apropos, of nothing' added the concept to the website 'Urban Dictionary'.

2/ dickrolling led to a period where the vital 18-35yo demographic shunned the internet entirely, and this set the final death knell for floundering website Twitter.

3/ in spite of the anger and upset caused by the "dickrolling fiasco" ;as it came to be called, the younger generation, no longer distracted by the internet, got out and voted and managed to avoid an inexorable slide into fascism and civil war.
by Apropos, of nothing November 5, 2022
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