Another car whose year range I'm currently trying to break down.

1997: Introduction in late 1996. Trims: SE, Country, Limited and of course Sport.

1998: The Classic is reintroduced after a year of absence, replacing the Country. Slotted below the Limited, it can be identified by painted bumpers and lack of fog lights.

1999: Roof rails modified. I put this in bold as it's a very important change. They now only go up to the B pillar as opposed to stretching the entire length of the roof. The Sport now sports a painted grille and central rear bumper section, and a badge on the door instead of a decal on the fender.

2000: New 'Icon' wheels available on Limited and Classic (tinted on the latter) . Limited now has a chromed liftgate.
The Ecco wheels are available on the Sport for the first time this year. The very rare Freedom Edition is introduced.

2001: SE discontinued. The 60th Anniversary Edition is introduced. All Cherokees have tinted windows this year.
Towards the end of the 2001 MY, the Classic gets a new door badge with a small rectangular badge as opposed to the previous script. This change was applied sometime around October or November 2000, the views on Copart of this badge aren't all that good.

@Gamer Looks like another mid-year change on the roof-rack. That brochure for 1999 clearly has the longer roof rails present.

The 1998 & 1999 brochures list the roof-rack running the full length of the SUV.

1998 full lineup brochure: http://www.auto-brochures.com/makes/Jeep/Jeep_US20Line_1998.pdf
1999 full lineup brochure: http://www.auto-brochures.com/makes/Jeep/Jeep_US20Line_1999.pdf

Here's a discussion about it on a Jeep forum:

https://www.jeepforum.com/forum/f11/97-01-xj-roof-rail-dfferences-1254461/

Here are some of my Jeep XJ Cherokee notes:

1984: 10-slot grille
trim levels are base/Pioneer/Chief

1985: Laredo trim introduced
Chrome bumpers
Euro LHD version
2WD version introduced
Turbo-diesel model introduced

1986: nothing

1987: 4.0L introduced
Limited trim introduced mid-year

1988: New 8-slot grille
Sport 2-door introduced
Pioneer Olympic trim (one year only)

1989: Sport wheels discontinued
Anti=Lock Brakes introduced (ABS)

1990: Rear 3-point seatbelts introduced (can see hanging from rear window)
Last year for chrome bumpers, Chief trim and 4.0L

1991: Roof Rack change
4.0L High Output engine introduced
Briarwood trim and Sport 4-door introduced

1992: (I have Euro model but I have to look up what I meant by that)
First year for official police package
Last year for Base, Briarwood, Laredo and Limited trims

1993: SE and Country trim introduced
4x4 decal replaces raised logo on rear fenders
Sport body clad change
UK models introduced

1994: CHMSL added
Country in silver

1995: Airbag

1996: Classic trim introduced for one year

1997: 7-slot grille
smooth tailgate
larger mirrors
wheel well change
Last year for Country trim
Spare tire moved inside

1998: Classic & Limited trims brought back

1999: Sport models get color-coded bumpers and grilles

2000: Limited gets more chrome

2001: 60th anniversary model introduced

Very important change for late 1985 - the positions of 'Jeep' and 'Cherokee' badges were swapped. 1984 and early 85 have Cherokee on the liftgate and Jeep on the lower right quarter of the trunk, this was vice-versa from late 1985 onwards, hence why you rarely see any Cherokees with the model name on the lift gate.

And in the latter half of the 1987 model year the Chiefs got new cladding.
1984-87.5: http://www.2040-cars.com/_content/cars/images/29/972829/001.jpg
1987.5-1990: http://www.2040-cars.com/_content/cars/images/33/900933/001.jpg

Also I don't think 1990 was the last year for chrome bumpers as they are still illustrated in the 1991 brochure: https://www.picclickimg.com/00/s/MTIwMFgxNjAw/z/ru4AAOSwVehcmn
And in 1992 as well: https://www.picclickimg.com/00/s/NjQxWDEwMDA=/z/ApUAAOSwqpBdZXCY/$/1992-Jeep-Book-Sales-Brochure-Wrangler-Cherokee-Comanche-_57.jpg

Yeah, I noticed I have some pics up to 1996 with them, it must have been a note for a specific trim and not the whole line

1991: Laredos receive silver bumpers with silver caps as opposed to the previous unpainted steel (probably to fight off corrosion better)
The Limited's script is changed this year from cursive to block font. The gold crosswire wheels, available from the start, mysteriously vanish this year and are replaced by body-colored wheels. The gold wheels return in 1992.

Found a few Cherokees with this odd badge placing: https://www.copart.com/lot/45397077

I can't quite get my head around it. It's got the 4.0 so why isn't that badge on there?