If you have all your music, masterfully ripped at high quality on your iPod, and you still haven’t hooked it up to your car’s sound system, what a waste! It’s an easy step to take once you know the direction to go. Here’s a run-down, from worst to best, of the ways to link your iPod, other digital music player, or portable CD player to your car’s “head unit,” the industry’s fancy term for “radio”.
An FM modulator is a low-power FM transmitter that broadcasts on an unused frequency. You plug a connecting cable from the modulator into your music player’s headphone jack. Most of the portable satellite radio tuners from Sirius and XM have modulators built in, and usually run $20-$30. They work on every car with an FM radio and you can choose from multiple frequencies. They’re also affordable and most don’t require installation. However, quality ranges from okay to poor. For models that don’t plug into the lighter, you must remember to bring a spare AA or AAA battery.

You can plug in a cassette adapter (since the 1980s and the first portable CD players) to your car’s cassette slot, and press Play. It works adequately if you, ah, still have a car cassette player. They cost about $10 to $20 and work with every car with a cassette player, but they produce merely adequate sound quality.
An FM modulator with an antenna direct connection transmits, but not over the airwaves. You insert the car radio antenna plug into the back of this modulator, and the modulator’s antenna plugs into the back of the car radio where it directly injects the signal. Sound quality is better, and less variable, than with other FM modulators. Cost is $30 to $75 and you may want an audio shop to install it. Check out products from Fahrenheit and Scosche, among others. They produce adequate to good sound quality and draws from car power, requiring no batteries. They may need professional installation (not hard). A handful of esoteric cars may lack the standard antenna jack or it will be in the trunk (requiring extra wiring).

A line-in connection works by running a cable from the headphone jack of your music player to a jack on the front of your car radio, a music-in jack in the glovebox, or in the center console. Automakers only got religion in the last year or so, and a few started adding line-in jacks, although others, like Lexus, will charge extra for it. Before, they (or the dealers) thought you’d be willing to pay $500 for a trunk-mounted CD changer that would play six CDs. Look for a stereo line cable with 1/8-inch jacks at both ends; this is the common size for music player headphones. They cost is $2-$10 and produce excellent sound quality but few cars have line-in jacks as of yet.
Next is the line-in connection via CD changer. Most cars built in the past decade have a jack in the trunk for the dealer-installable CD changer you never bought. Or a CD changer connector on the back of the factory radio. If your car lacks a line-in jack and you want best sound quality, this is where you make the connection. Sound quality won’t be any better or worse than a standard line-in connection, but this may be the only way to hack in. Some trunk-mount satellite radios can actually pass track-and-title information to the radio head unit. Cost varies from $25 to $150 plus an hour or two of installation time. It may be possible to have both a satellite radio and a music player connected with a custom A/B switchbox. These produce an excellent sound quality and it’s possible to pass satellite radio station, song information to car radio. They are not cheap though, and may require disconnection of CD changer if you have one.

iPod smart-cables or black box (actually silver box) modules specific to Apple’s all-conquering iPod connect into the CD changer jack or the back of the radio’s CD changer/satellite radio jack. They pass the signal to the radio and charge your iPod at the same time. Some modules pass artist, track, and title information to the car radio. Others (Harman/Kardon drive+play, Monster Cable iCruze) have their own small LCD panels that mount on the dash, replacing the display of your iPod, which can be safely stashed in the glovebox. Costs range from $100 to $250 and provide excellent sound, battery recharge, (sometimes) song information passed to car radio or dedicated LCD panel. The downsides are they are costly and require complex (for you, not the shop) installation. They disable iPod faceplate/controls, and may limit you to a half-dozen playlists with specific names.