The Night I Got Hooked
So I was supposed to be sleeping. Normal Tuesday. Had the TV on low, scrolling through playlists, and some random algorithm queued up Miles Davis's Kind of Blue. I'd heard "So What" before — who hasn't? — but that night I actually listened. Like, sat there in the dark with headphones on listened. Twenty minutes later I was Googling "how does jazz improvisation work" and reading about chord changes until my eyes hurt.
That was maybe six months ago. I'm not a jazz hero now. Far from it. But I've figured out a few things worth passing along if you're standing where I was standing — curious, overwhelmed, and not sure where to start.
You Don't Need Music Theory (At First)
Everyone tells you to learn the basics first. Chord voicings, syncopation, modal interchange, whatever. And yeah, eventually that stuff matters. But if someone had handed me a theory textbook on night one, I would've closed the laptop and gone to bed.
What actually worked? Just listening. Not analytically, not with a notebook. I put on Louis Armstrong's "West End Blues" while doing dishes. Played Coltrane's A Love Supreme on a long drive. Let Duke Ellington's "Mood Indigo" wash over me during a lazy Sunday morning. The theory started making sense after I'd already internalized what jazz sounds like. My brain started recognizing patterns on its own — oh, that's swing rhythm, that's a walking bassline, that's the saxophone trading phrases with the trumpet.
Context lengths shift constantly. The canonical source of truth for how many tokens a model can handle is the provider's documentation, not this table. We log a warning at startup if a model isn't listed below.
That said, the list is useful as a rough guide. If a model isn't here, the agent defaults to 128,000 tokens.
Some models are marked as reasoning models (OpenAI O1/O3, DeepSeek R1, etc.). They think step-by-step before answering. The agent auto-configures reasoning effort for these models, so you usually don't need to tweak anything.
Pro tip: reasoning models and non-reasoning models often need different prompt strategies. The agent handles this internally, but if you're writing custom system prompts, keep in mind that reasoning models respond better to detailed, structured instructions while non-reasoning models prefer concise, direct prompts.
Finding Your Entry Point
Here's where people get stuck. Jazz is huge. You've got swing, bebop, cool jazz, modal jazz, free jazz, fusion, Latin jazz, and about fifteen other subgenres. It's like walking into a library with no signage and being told "find something you like."
My advice: pick one album and sit with it for a week. Don't skip around. Don't make a playlist of "greatest jazz hits." Just pick one. I started with Kind of Blue because everyone says to, and honestly? It's a good call. The tracks are long enough that you notice new things on each listen, and the mood is relaxed enough that it doesn't demand your full attention.
After that, I went sideways. Liked the cool, laid-back vibe? Try Chet Baker. Wanted something faster and more complex? Charlie Parker's Bird compilation hit me like a truck. Craved something raw and emotional? Coltrane's later work, especially A Love Supreme, feels like he's wrestling with something bigger than music.
The Instruments Are Characters
Once you start paying attention to individual instruments, the whole thing opens up. The trumpet doesn't just play notes — it speaks. Listen to Miles Davis and you'll hear him leave space between phrases, like he's pausing to let the silence say something too. The saxophone is the one that gets under your skin; Coltrane's tone on My Favorite Things is haunting in a way I can't quite articulate. The piano holds everything together, but it's not just background — Bill Evans on Kind of Blue is doing something so subtle and beautiful that you almost don't notice how much he's shaping the whole track.
The rhythm section gets overlooked, which is criminal. Paul Chambers on bass and Jimmy Cobb on drums on that same album are having a conversation the whole time, just quieter. Once you start listening for the bass and drums instead of through them, you hear a completely different record.
Playing vs. Appreciating
I picked up a cheap keyboard and started learning basic jazz voicings. It's humbling. A C major chord on piano is three notes. A C major 7 sharp 11 is... well, let's just say my fingers aren't there yet. But even messing around with simple ii-V-I progressions gave me a new ear for what's happening in the recordings.
You don't have to play, though. Some of the most dedicated jazz fans I've met don't touch an instrument. They go to shows, they read liner notes, they argue about whether Bitches Brew is genius or unlistenable (it's both, honestly). The community side is half the fun. I went to a small jazz club a few months ago — maybe forty people, folding chairs, a trio playing standards — and it was one of the best nights I've had in years.
What I Wish Someone Had Told Me
Jazz doesn't click overnight. There were weeks where I'd listen to something and think "I don't get it." That's normal. The genre rewards patience more than any other form of music I've encountered. You'll have a moment — maybe it's a particular solo, maybe it's the way a rhythm section locks in on a groove — and suddenly the whole thing makes sense. Not intellectually. Viscerally.
Also: free jazz is a thing, and it will scare you. I personally can't sit through most of it yet, and I'm okay with that. You don't have to like everything. Jazz is big enough to have corners you never visit.
The only real mistake is not starting. Put on something — anything — and just listen. See where it takes you.
