Reader question:

What does this – He's from the old school, fool – mean?

My comments:

Ha, it means the speaker is not very fond of "he" who is from the old school. The speaker considers him foolish, perhaps not in the straightforward¹ stupid, unintelligent way, but in the way that the old-school man might be intolerably inflexible². Just a guess.

First, definitions. Someone who is "from the old school" is one brought up and trained the traditional way. He has conventional ideas and ways of doing things. For example, the painter from the old school might have a difficulty appreciating the avant-garde. In music, he may prefer classical music to, say, rock 'n' roll and rap.

"Old school" is not a derogative³ term. The term itself is mutual⁴. In "he's from the old school, fool", it's a putdown, but in "he's from the old school – he's impeccable in speech and behavior", for example, it is a compliment.

Also, it's the same thing to say someone is "old school" (the coach is old school – he trains us three times a day) or "from the old school" (the teacher is from the old school – he never tires correcting our pronunciations).

And, by the way, "old school" has nothing to do with your Alma Mater, that is, the old school you graduated from.

Here are a few examples from the media. But before the examples, let me say happy holidays to you all. Guo Nian Hao!

Examples: 

1. For his most recent single, "Feel It," Erick Sermon didn't invite the reggae vocalist Sean Paul into the studio to sing the song's chorus. Sermon didn't even call Paul — he just sampled him instead.

Owing to the high cost of samples, mainstream⁵ hip-hop producers do very little actual sampling these days, but Sermon, an ambassador from the old school, still relies on such tried-and-true methods for his solo career.

- Erick Sermon Keeps It Old-School, mtv.com, June 29, 2004

2. Gar Heard calls himself an old-school guy. He believes rookies should carry the bags of veterans. Heard also benches people, regardless of their reputations or the size of their contracts. He rarely raises his voice. Heard, the first-year coach of the Washington Wizards, treats players like professionals, unless they deserve otherwise. He coddles no one. Here's his one departure from the old school: He doesn't believe in fines; he believes in benchings. Guys make too much to care about fines, he says. Burying them gets their attention…

Old-school methods. Maybe it works.

- Heard is giving the Wizards the old-school treatment, Sporting News, August 11, 1999

3. If there is an engineer on site, is it better that he is from the old school, who understands the plant equipment from having stood next to it, worked with it, and seen the faults that develop: or from the new school, who understands the diagnostic messages transmitted over the fieldbus into the IT system?

- Finding experienced freelance process engineers, Processingtalk, November 9, 2007