This activity was once a very popular pastime of the poor and the nerdy.

Some who did it became famous,

while some became infamous:

In fact, it became quite a significant cultural phenomenon, managing to get references in Hollywood:

What activity is this that became a “classic” pastime? Who’re all these guys? (The pictures are full of clues )

Partially cracked by: Biki , srichand , Goutham , Mighty Anon , jayanth , shivani , Poornima , and Gammafunction. I’m feeling generous again.

The complete answer I was looking for:
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This question is inspired by a suggestion from Nihit.

What is 1′s demo of 2 popularly known as? And identify 1 and 2 please.

1.
2.

Cracked by: srikanth , Sharath , udupendra , uma , jayanth , yaksha , alephnull , Poornima , Shashank.

Many others got very close.

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First featured on screen in 1, popularly shown in 2 and claimed to have been shown in 3.
What?

1.

2.

3.

Hint: Look closely in 2 :)

Prasad , bs , ramsaravana , Abhishek , Sharath , uma , Tathagata Chatterjee , udupendra , piezocake , Mahesh Herle , Gammafunction , yaksha , Shashank “hacked” the answer. :)

2ndratequizzer got close.

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What is this? And what is its claim to fame?

this may help a bit more

Unearthed by: Abhishek , ramsaravana , nihit , Gammafunction , Vinod , uma , Sharath , Swetha , Arjun June , Tathagata Chatterjee , shivani , yaksha , srichand.

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Connect and explain

1.

2.

Cracked by a good bunch of people: udupendra , Vinod , pratap , ramsaravana , shyam , Piyush , Sharath , Mahesh Herle , nihit , Goutham , Abhishek , yaksha , Arun Krishnamoorthy , Arjun June , uma , Archana , Shashank.

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Connect the 3 books to another:

bs , Ramanand , ramsaravana , nihit , Arun Krishnamoorthy , Sharath , BiGFooT , udupendra  and jayanth cracketh  the Q.

Answer:
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Connect

1.

2.

3.

Cracked by udupendra and nihit. Nice work!

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Created by this founder of Infocom (pic 1), it became an integral part of geek culture, and now regularly appears in nerdcore music (2) and comic strips (3). What?

1)

2)
3)

Basically, fill in the part of the comic that’s blanked out. (Identify the guy in 1 too)

Uudupendra , nihit , prasanth , Archana , sumanthvanahalli , yaksha , BiGFooT , Mahesh Herle  and Shashank have taken the first steps on the road to being Master Adventurers.

Answer:
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1.

2. ?

3. 4.

1 lead to 2 ( no, there is no image there ), which in turn led to 3 and 4.
What is 2?
While you are at it, put fundas about 1,3 and 4 also

udupendra , Arun Krishnamoorthy , srikanth , prasanth , yaksha , Abhishek got it almost right.

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Connect the three images below to an iconic system:

(Detailed fundas on all three preferred)

Cracked by: udupendra , Arun Krishnamoorthy , Biki , nihit , Shashank and Ganesh Prasad.

Answer:
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