Sam and Max Hit the Road
I first saw this game on television on some early nineties video game show that was on during Saturday mornings. I was lured over by the cartoon style and the dry sense of humour and fell in love after playing the demo at my friend's house that he got from a PC Format Gold disc that had heaps of shareware and demo games on it. Still the best Sam and Max adventure in my opinion and I just love the characters and the world - it's like Raising Arizona meets Duckman.
My second adventure (following the theme of this thread) was the CD-Rom version of Leisure Suit Larry 6 and that series became a huge obsession of mine. I still have a boatload of related paraphernalia to that franchise. My only gripe was that I wasn't old enough to buy an old cardboard cutout of Larry I saw in a computer store promoting the seventh game. (Come to think of it, I am impressed I was able to talk my mother into buying me Larry 7... I was 14/5 at the time.)
EDIT: This reminds me... My younger brother who was 5/6 at the time actually recognized Larry's Greatest Hits and MIsses in a electronics store having seen me play Larry 6 briefly, before I had to remove him from the room, and had my father buy me the collection who was none the wiser. Best brother ever.
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