I received my license when I was 17, and immediately took my first solo drive to Old Fullerton Road.
I drove there in my first car, a 1972 Volvo 164 F/E.
Not much of a canyon, not a very quick car, but such was my start.
A few years later I dated a girl who owned a 1991 Toyota Tercel.
A lowly car, indeed, but it had a four speed manual, and I learned to shift my own gears in that car. I also drove it more than she did. Nearly every night, after droping her off at her parent's house, I would drive up the road to Santiago/Trabuco Canyon, and have a blast.
The Live Oak Canyon turn off, was my favorite part. Around midnite, I had the canyons pretty much to myself. The Tercel had no power to speak of, but it also weighed very little. It was a hoot in the twisties.
A year or so later, I bought a 1985 Nissan Sentra fastback from a friend for $500. An automatic, and not a fast car, but I was poor. I proceeded to drive this around the country, mostly in Colorado. I drove in and around Colorado Springs, on and off-road, (What else do ya do with a beater?) Lots and lots of driving on US24 and US50. Most of the offroad was around 11 mile reservoir and Rainbow forest. I also drove my buddy's 1989 Ford Ranger 5spd a bunch around this time and area.
After joining the Marine Corps and getting married, I bought a 1997 Jeep XJ, (The little Cherokee,) Which I still own and drive.
We bought the 2 door, 2 wheel drive, 5 speed model. The only options we got were cloth, (Instead of vinyl,) seats and the 4.0L inline 6, (A/C was standard.) This little "SUV" weighs just under 2900 lbs. That's right, it is 62 lbs heavier than Honda's S2000. 225ft/lbs of low-end torque in a sub 2900 lb package almost makes up for the leaf-spring suspension and solid front and rear axles. But I didn't buy this for hitting the canyons. Nevertheless, I drove Banner Grade up to Julian on the way home from Yuma, AZ plenty of times. I still hit up Highland Valley Road, (Which I live nearby now,) in the XJ every once in a while.
In April, 2001, I managed to con one of my friends into loaning me his battered '96 YZF600R so I could take the MSF course. In June 2002, when I came home from Operation Enduring Boredom, I bought an '02 Suzuki SV650S in silver. I gained a whole new perspective on canyons.
By far, my favorite hillclimb on the motorcycle is the legendary South Grade Road, better known as Palomar.
Around late 2003, it was becoming clear that we needed a new car. The Jeep was a tad bit long in the tooth, and had suffered the ravages of two infants and the Arizona sun. We decided on the Mazda 6s, narrowly beating the Saab 9-3 and Infiniti G35 sedan, mainly on price/features. I have since regretted buying the Mazda, but it has its good points.
220hp 190ft/lbs torque, but that's pretty high in the rpm range, so despite being a 3.0L V6, you still need to keep it singing. It weighs 3300 lbs, so it can be a bit of a bear in the mountains. It likes to push, but it is pretty forgiving if you give it slight inputs. The throttle is drive-by-wire, so it is a bit too laggy for heel-and-toe, IMO. After learning to ride a motorcycle, I don't use heel-and-toe, anyway, because I set up for the turn and engine brake, then accelerate throughout the turn. I am less of a driver for not trail braking or using heel-&-toe downshifting, but I rarely go 10/10ths, anyway. (Certainly little incentive in taking a 3300 pound beast, which also happens to be the car that the family relies upon, to 10/10ths.)
Now, in 2006, I am out of the Corps and workign as a delivery driver/courier by day and a Mobile Notary by night. I serve all 6 southernmost California counties, (San Diego, Imperial, Orange, Riverside, San Bernardino, Los Angeles,) and parts of Ventura. Since I often find myself coming home at late hours, (When canyons are mercifully free of communters,) I avail myself of the oppurtunity to have some fun.
Recently I have discovered the joys of Tuna Canyon Road, (though my Mazda is far too heavy to attack that road with any speed,) and the surrounding area.