• Turntable ★ Unless by the off chance he decides to be a dj
• Albums ★ See above.
• .45's ★ See above.
• A Dial Up Modem ★ Im crushed that he will never experience the joyous handshake sounds and blazing 14.4kbps speeds.
• Drive In Theater ★ They were barely around when I was a lad, so he definitely won't be going to the drive-in. I still think a "new" retro drive-in would be a hit with todays gen.
• Rooftop TV Antenna ★ Another victim of progress.
• School Paddeling ★ No Board of Education for him. I think that's sad.
• DOS ★ Or any other command line interface for that matter. Nope all pointy clicky from here on.
• Mailing Of Letters ★ I wanted to a postman growing up. Will he even know what that job was?

And finally a suggestin from EstroJen in the comments section, thanks Jen!

• Phone Boothes ★ Whats Superman gonna do if all these go away?