I really only remember from about 1984 on, but I can give a good guess before that. So here's my stab at it:
1. 1985 (91-71, World Series Champions)
We might as well start with the obvious, right? (It's not hard to figure out number one.) Not only did the Royals win the World Series that year, they did it in dramatic, comeback fashion with a great mix of old favorites (George Brett, Frank White, Willie Wilson, Hal McRae, Dan Quisenberry) and newer stars (Bret Saberhagen, Danny Jackson, Steve Balboni, etc.). Brett was denied the MVP despite leading this light-hitting team to the title with a .335 average, 30 HR, and a Gold Glove at third base. Balboni hit a franchise-record 36 home runs, Charlie Leibrandt was second in the league in ERA, and Saberhagen captured the Cy Young with 20 wins.2. 1980 (97-65, American League Champs)
I know, it doesn't take brilliant analysis or insight to rank '85 and '80 as the two best seasons to be a Royals' fan, but we got the two easy ones out of the way first. This was George Brett's .390, MVP season. Willie Wilson played like a Hall of Famer. They finally got past the Yankees. This year probably had more pure excitement than '85, but the World Series disappointment puts this year in second place.
3. 1977 (102-60, AL West Champs)
This was the Royals' best regular season. They had a record-breaking run to end the year, only to be disappointed again in the playoffs. This was Al Cowens' big year (.312, 23 HR 112 RBI) and George Brett's first big HR year (22 in '77, 20 career HR before '77). It was also Darrell Porter's first year with the club, Dennis Leonard's first 20-win season, and the year that Jim Colborn managed to win 18 games.
4. 1976 (90-72, AL West Champs)
The Royals' first division title came in 1976. This was the year that George Brett and Hal McRae finished 1-2 in the batting race (back when that was a really big deal). Brett, McRae, and Amos Otis finished 2nd, 4th, and 7th, respectively, in the AL MVP voting. This team wasn't as good as the '78 division-title team, and they had a worse record than the '75 team, but there's something special about that first playoff team, especially since they came within a Chris Chambliss home run of the World Series. It was a heartbreaker to be sure, but as Royals fans would eventually learn, it's better to have your hopes crushed than to never have hope at all.
5. 1978 (92-70, AL West Champs)
It was the Royals' third division title in three years, and for the third time in a row, they lost the ALCS to the Yankees. Unlike the previous two seasons, this series did not reach the maximum five games. Negatives for this season would be the continued playoff frustration and the 10-game drop-off from '77. But they still won the division, Amos Otis finished 4th in the MVP race, and Al "The Mad Hungarian" Hrabosky was their bullpen ace, so this season was still a lot of fun for Royals fans.
6. 1984 (84-78, AL West Champs)
The '84 Royals weren't all that good, especially for a division winner. They were, in fact, outscored by their opponents and then quickly swept aside by the Tigers in the ALCS. No doubt many of the Royals teams that did not win their division were better teams than this one. But this is a list measuring how fun it was to be a fan, not the quality of the teams, so this squad earns this spot. They took advantage of a weak division (no one else in the AL West outscored their opponents, either) and rode a reworked pitching staff to the division title. Dan Quisenberry finished 3rd in the MVP race and 2nd for the Cy Young with a 44-save, 129.1-inning season. Bud Black had his finest season as a Royal, leading the team with 17 wins, and Charlie Leibrandt, Danny Jackson, Mark Gubicza, and 19-year-old Bret Saberhagen all made their Royals debuts. It's fun to be a fan of a team that wins close games, has good young players, and wins their division, and that's why it was good to be a fan of the '84 Royals.
7. 1982 (90-72, 2nd place AL West, 3.0 games back)
It was hard coming up with the year that was most fun for Royals fans where the team failed to win their division. I chose 1982. This was a good Royals team led by its historic stars (Brett, McRae, Wilson, White). They coughed up the division with a 7-game September losing streak, but there were a lot of elements that made this team a lot of fun: Willie Wilson won the batting title at .332, Hal McRae drove in 133 runs and finished 4th in the MVP race, John Wathan set the stolen-base record for catchers with 36, George Brett had a nice year, and it was also a big year for the immortal U.L. Washington (.286, 10 HR, 23 SB), the shortstop known for the toothpick perpetually hanging from his bottom lip.
8. 1989 (92-70, 2nd place AL West, 7.0 games back)
There was a lot to love about this team, and it really all starts with Bo Jackson. This was Bo's breakout year, complete with the All-Star Game bomb and MVP award, the "Bo Knows" commercials, and the 105-RBI season. It was also the year Bret Saberhagen turned in his best season, which was the best season ever for a Royals starter, winning the Cy Young with a 23-6 record and a 2.16 ERA. Tom Gordon was a rookie phenom, winning 17 games between the bullpen and the rotation. It might have been the Royals' best team that didn't win a division, but the problem was that they never really got all that close to the dynastic A's. They never led the division by themselves, and they never got closer than 2.5 games out in the last two months of the season. When a 9-game winning streak near the end of August only gained them 2 games in the standings, their division chances really died. It was a fun season to root for the team, but ultimately, it was more about their stars than any chance at a team championship.
9. 1975 (91-71, 2nd Place AL West, 7.0 games back)
The Royals really didn't compete in 1975, but they finished with a strong enough kick under new manger Whitey Herzog (who replaced Jack McKeon midseason--which really puts into perspective how old McKeon was when he won the World Series with the Marlins in '03. Wow.) This season hinted at the great run that was coming over the next 5 seasons. This was George Brett's first year as a really good player, and John Mayberry (.291, 34 HR, 168 OPS+) was at his best this season as well. And hey, there was also DH Harmon Killebrew. (Well, his .199 average wasn't probably very fun to watch, but he was an all-time great making his last stop).
10. 1973 (88-74, 2nd place AL West, 6.0 games back)
In just the fifth year of the franchise, the Royals lasted into mid-August as legitimate contenders for the division championship, finally relinquishing first place for good on August 17th. John Mayberry and Amos Otis both started the All-Star Game, Otis finished 3rd in the MVP vote, Paul Splittorff won 20 games, and Steve Busby threw his first no-hitter.
11. 1981 (50-53 overall, 30-23 2nd half, 2nd half AL West champions)
I wasn't old enough to really know about 1981. It's a hard one to rank because on one hand, they came off their best season to date and posted a losing record overall, George Brett went back to playing like a mere mortal, and the strike robbed all fans of a third of the season. In that light, this season is probably rated too high (It was, after all, enough of a bummer to get Jim Frey fired). But on the other hand, their post-strike surge under Dick Howser earned them a playoff spot as the "2nd half champions" under the goofy system set up by commissioner Bowie Kuhn. So maybe since they made the playoffs, I should rate it up with the playoff seasons. But they got swept out of the playoffs in 3 games, scoring all of 2 runs in the process, so I wouldn't think this season deserves to rate any higher than here. Taking the general bummer of the strike into account as well, there's a very good argument to knock this season down a few notches from here.
12. 2003 (83-79, 3rd place AL Central, 7.0 games back)
Creemos! Tony Pena won the Manager of the Year award this year for seemingly rah-rah-ing this team into 92 days on top of the division. It was all smoke-and-mirrors, of course, but it was fun while it lasted. There was debate in the preseason magazines and season previews as to which AL Central team was more pathetic: the Royals or the Tigers. The Tigers went on to lose 119 games that year, and the Royals started off 9-0, then 17-4. They were up 7.5 games on July 17th (6.5 on July 19th, my wedding day). It was a weird, weird season: Opening Day starter Runelvys Hernandez started the season 4-0 with a 1.10 ERA. Before taking the mound the day he got hurt on May 14th, his ERA was 2.04. Jose Lima started off 7-0 with a 2.17 ERA in his first 8 starts after getting picked up off the scrap heap. Chris George managed to go 9-6 despite a 7.11 ERA. Angel Berroa was good! He won the Rookie of the Year with a .287, 17-HR, 21-SB season. They faded at the end, and they were eliminated when Lima and the Royals lost to those 119-loss Tigers (and 21-game loser Mike Maroth) on September 23. It was fun, but who among us really believed that year?
13. 1979 (85-77, 2nd place AL West, 3.0 games behind)
The Royals were a good team that contended all year in 1979, but much more was expected of this team. The problem was a starting rotation where everyone had a down year. Highlights were great seasons from George Brett and Darrell Porter and the fulltime debut of Willie Wilson, who hit .315 and stole 83 bases. The Royals were in first place as late as August 30th, but the disappointing finish cost Whitey Herzog his job.
14. 1971 (85-76, 2nd place AL West, 16.0 games behind)
In just their third season, the Royals posted a solid winning record and finished second in the division. The shine of a new franchise starts to wear off by year three, and the Royals picked up their game just in time. But their 2nd place finish belies the fact that they were never really in any sort of contention. They never were closer to Oakland than 10 games back after July 2 (and it had to sting a little to see Charlie Finley's A's who just moved from KC a couple of years ago win 101 games). Amos Otis was their best player, hitting .301 with 52 steals and finishing 8th in the MVP vote.
15. 1994 (64-51, 3rd place AL Central, 4.0 games back)
The two strike years are the hardest to figure. 1994 was the was the last Royals team that was actually good (not fake good, like the '03 team). "The Hammer" (Bob Hamelin) was the Rookie of the Year, and Royals fans waved big blue foam hammers as they cheered the Royals on a 14-game winning streak at the end of July going into early August. David Cone was the Cy Young winner. But how can any season rate highly when it was cut short? The fun through August 10 probably would put this team a few slots higher, but the crushing blow of the strike (and what it would mean for the Royals franchise thereafter) might even call for this one to rank near the bottom.
16. 1993 (84-78, 3rd place AL West, 10.0 games back)
This team contended for a while and was in first place as late as July 6, then faded. It was George Brett's last year, and he went out showing a little more pop than in recent years (19 HR), and he went out with a solid base hit up the middle in his last AB. Kevin Appier (18-8, league-leading 2.56 ERA) should have won the Cy Young, and Jeff Montgomery won Fireman of the Year with 45 saves and a 2.27 ERA.
17. 1988 (84-77, 3rd place AL West, 19.5 games back)
After a couple of down years and a move to first base, George Brett was back to being an elite player in '88 (.306, 24 HR, 103 RBI, 14 SB). Danny Tartabull and Bo Jackson were good that year, and it was Mark Gubicza's big season (20-8, 2.70). Bill Buckner got too many starts at DH. (Wait, Bill Buckner was on the Royals? I guess I have a vague recollection of that.) The team never contended, spending most of the season in 3rd or 4th place.
18. 1987 (83-79, 2nd place AL West, 2.0 games back)
'87 was the Billy Gardner Royals, the year Dick Howser died. This season was a bummer for a few other reasons, too. Bret Saberhagen went from 15-3 with a 2.47 ERA on July 11 to an 18-10, 3.36 ERA finish. The team that beat them, the Twins, were not a good team. Dan Quisenberry lost his closer's job and only saved 8 games. Angel Salazar (23 OPS+) was their regular shortstop and Larry Owen (50 OPS +) was their near-regular catcher. They were two games ahead going into a series in Minnesota July 8-10; they were swept and never really threatened the Twins again. They got above .500 and within two games of first with a garbage-time surge in the last two weeks, gaining 4 games in the standings after they were eliminated. (Also, they traded David Cone for Ed Hearn before the season and Danny Jackson for Kurt Stillwell shortly after). So despite a great rookie year from Kevin Seitzer, a really good Royals debut by Danny Tartabull, and the arrival of Bo Jackson, this season was a definite downer. I guess it's a personal preference thing, but this team irritated me, so despite contending better than in some of the years listed ahead of this one, this season ranks, to me, as the one of the worst season to be a Royals fan out of their winning seasons.
19. 1969 (69-93, 4th place AL West, 28.0 games back)
The expansion year of a franchise is kind of a free pass. It's like it's spring training all year long, especially when the team isn't nearly as bad as other expansion teams have been. The '69 Royals were one of the best first-year expansion teams in baseball history. They spent the first couple of weeks of the season in first place, and they didn't fall below .500 for good until May 14th. Lou Piniella won the Rookie of the Year. It was as nice a year as a 93-loss year can be, I think.
20. 1991 (82-80, 6th place AL West, 13.0 games back)
This was the year that no one in the AL West finished with a losing record. The Royals spent most of May, June, and July in last place. The closest they got to contending was 4th place, 6.5 games back, in mid-August. It was Danny Tartabull's best year, but you knew he was leaving as a free agent after the season. George Brett hit .255. They released Bo Jackson before the season started because of his football injury. So despite the winning record, this was a "blah" year for Royals fans.
21. 1972 (76-78, 4th place AL West, 16.5 games back)
After finishing with a winning record in '71, the '72 team took a step back, falling just short of .500 in a season shortened somewhat by a players' strike. 1B John Mayberry, acquired from Houston in an offseason trade, had a great Royals' debut, hitting .298 with 25 HR and 100 RBI.
22. 1995 (70-74, 2nd place AL Central, 30.0 games back)
There was a lot to hate about being a Royals fan in 1995. Ownership reacted to the '94 strike like they needed to go out and prove that they couldn't compete as a small market. They traded David Cone and Brian McRae for nothing, let Mike Mcfarlane walk as a free agent and then fired Hal McRae for no particular reason and hired Bob Boone. On the field, Tom Goodwin and Brent Mayne were starters, and so was Bob Hamelin, who followed up his rookie year with a .168 average. When they DFA'd Vince Coleman in mid-August despite being in wild card contention to install another rookie (Johnny Damon), they seemed to be throwing up the white flag. But it turned out to be the right move. Damon energized the team and played very well. They surged into the Wild Card lead and stayed there until September 8th. Damon and the Royals faded badly from there. They finished 9 games off the Wild Card pace, and from there the Royals initiated their descent into being one of the very worst franchises in baseball.
23. 1970 (65-97, 4th place AL West, 33.0 games back)
The team took a small step backward from their expansion year, but Amos Otis joined the team and had a nice year, Bob Oliver had a big year (99 RBI), and Lou Piniella did what no other Royals Rookie of the Year has done: had a good second season. Year two of an expansion team still falls well within the grace period, and they managed to avoid last place. So for a season with 97 losses, this one wasn't so bad.
24. 1974 (77-85, 5th place AL West, 13.0 games back)
This was the first truly disappointing season in Royals history. After contending in '73, they stayed on the fringes of contention in '74 until late August. But then from August 30 to September 16th, they went 2-17, dropping from 2nd place, 4.5 games back, to 5th place, 13.0 games back. Bright spots were another no-hitter and a 22-win season from Steve Busby.
25. 1986 (76-86, 3rd place AL West, 16.0 games back)
The Royals followed up their World Series title with a stinker of a season, epitomized by an injury-plagued season by George Brett, a 7-12 season from Bret Saberhagen, and 34 appearances in the 3-hole by Rudy Law. At least Royals fans got to wear World Series Championship t-shirts all year.
26. 1983 (79-83, 2nd place AL West, 20.0 games back)
If you thought the Pine Tar Game was the coolest part of Royals' history, you'll have this year rated higher. But after that infamous game, the Royals fell apart a little (and more than that, the division-winning White Sox took off), and the Royals went from 1.0 game out of first to 20 games out by the end of the year. The pitching was a combination old, ineffective, and injured, except for the brilliant season from Dan Quisenberry. The worst part of this season was the embarrassment from the drug suspensions for Willie Aikens, Willie Wilson, Jerry Martin, and Vida Blue. (But some guy named Cliff Pastornicky played a few games at third for them, so there's that).
27. 2007 (69-93, last place AL Central, 27.0 games back)
One of the things that makes a bad season bearable is hope, and the '07 Royals gave fans some hope for this season and beyond, despite the fact that they were, by and large, pretty lousy. Alex Gordon and Billy Butler made their much-anticipated debuts; Joakim Soria and Brian Bannister were less anticipated, but they looked good. Gil Meche showed signs that his huge contract wasn't so ridiculous after all, and Zack Greinke rounded back into form. They avoided 100 losses for the first time since 2003, and they made Royals fans excited for the start of the '08 season.
28. 1990 (75-86, 6th place AL West, 27.5 games back)
One of the things that makes a season really lousy for a fan is unfulfilled hope. The 1990 Royals were coming off a 92-win season and had added National League Cy Young Award winner Mark Davis to the team, the first time in history a team had both defending Cy Young Award winners on their staff. Despite the fact that the A's had been one of the most dominating teams in years in '88-'89, many preseason publications dubbed the Royals as the best team in baseball. Then... Thud. The team spent all of one day over .500. The season would rate even lower if it weren't for some notable feats by some stars: Bret Saberhagen was the winning pitcher in the All-Star Game, Bo Jackson did most of his superhuman stuff this year (running up the wall, throwing out a runner from the left field corner on a line, calling timeout, not getting it, then stepping back in and launching a HR off of Jeff Ballard), and of course George Brett, who was hitting .256 on July 1, hit .386 the rest of the way to win his third and final batting title.
29. 2000 (77-85, 4th place AL Central, 18.0 games back)
It's hard for me to really distinguish between 1999 and 2000. Both teams really could hit, but really could not pitch. 2000 ranks here because the overall record was better (not that it was anything to get excited about). Mike Sweeney hit .333 with a team-record 144 RBI. Jermaine Dye was the starting RF in the All-Star Game. Johnny Damon hit .327. Mac Suzuki was their best pitcher.
30. 1999 (64-97, 4th place AL Central, 33.0 games back)
The thing that was neat about this year's offense was that it took you by surprise. Mike Sweeney was a catcher that they were going to cut so they could give the job to Chad Krueter, but Jeff King gets hurt, Sweeney takes over at 1B, and boom: .322, 22 HR, 102 RBI. Jermaine Dye's play over the past two seasons had been making Royals fans lament that they traded Michael Tucker to get him, then boom: 27 HR, 119 RBI. This was also the year of Dos Carlos (Febles and Beltran), with Beltran taking the Rookie of the Year with a 22 HR, 108 RBI season. Jose Rosado was back as a top-of-the-rotation starter, with a 130 ERA+. So in some ways, this season provided more hope than 2000, when everyone started living with the dread of the impending trade-off of all the offensive stars. This was the first year Bill Beane robbed the Royals (in the Kevin Appier deal). More was to come. But I'll keep this order, based on the difference in record.
31. 1996 (75-86, last place AL Central, 24.0 games back)
This was the first last place finish in franchise history. Mike Macfarlane was their best offensive player. Craig Paquette led the team in HR and RBI. Their most common 3-hole hitter? Keith Lockhart. Their most common 4-hole hitter? Joe Vitiello. (I'm not kidding). But only one batting order was used more than twice by Bob Boone, the magical Bip Roberts-Tom Goodwin-Johnny Damon-Keith Lockhart-Bob Hamelin-Joe Vitiello-Michael Tucker-Sal Fasano-David Howard combination (Yes, that's Lockhart in the 4-hole in that lineup; they went 1-2). But in the second half, their pitching front four of Kevin Appier, rookie Jose Rosado, Tim Belcher, and Chris Haney were legitimately good, giving Royals fans hope that if they could find someone to complement Keith Lockhart in the middle of their order, they just might be onto something.
32. 1998 (73-89, 3rd place AL Central, 16.5 games back)
What made being a Royals fan great in 1998 was Pat Rapp coming off the scrap heap to become a 90 ERA+ machine... or maybe it was marveling at the brilliant tactician Tony Muser pushing his team to outperform their Pythagorean record by eight games... or maybe it was watching Hal Morris make a run at .400 all the way into May. No, the best part was the scintillating run to 3rd place and the 73-win (and thus less than 90-loss) plateau.
33. 1992 (72-90, 5th place AL West, 24.0 games back)
You might say that any season from the George Brett era is better than any season from the Tony Muser era, and you really might be right. But the Royals buried their season in the first 2 1/2 weeks with a 1-16 start, and they just coasted from there as a mediocre team with decent pitching and terrible hitting. Kevin Appier had a great season replacing the traded Bret Saberhagen as the staff ace, but just about the only thing for fans to cheer this year was George Brett's 3,000th hit.
34. 2001 (65-97, last place AL Central, 26.0 games back)
Carlos Beltran and Mike Sweeney had nice years. Tony Muser was still the manager. They traded Jermaine Dye for Neifi Perez.
35. 1997 (67-94, last place AL Central, 19.0 games back)
To me, this was the first truly terrible Royals team. They looked like they'd have one of the better rotations in the league that year, but everyone but Appier was bad. The offense was absolutely brutal outside of two one-season rentals (Chili Davis and Jay Bell) and another guy who didn't project to be part of their long-term plans (Jeff King). They fired Bob Boone, but they hired Tony Muser.
36. 2002 (62-100, 4th place AL Central, 32.5 games back)
This was their first 100-loss season. Neifi Perez posted a 44 OPS+, but played good defense at shortstop. Chuck Knoblauch had a 50 OPS+ as a bad leftfielder. On a positive note, Mike Sweeney made a run at the batting title, Carlos Beltran and Raul Ibanez were really good, and Tony Muser was fired.
37. 2006 (62-100, last place AL Central, 34.0 games back)
The Royals didn't hire Tom Emanski that year, but maybe they should have. Mark Redman was their All-Star. They had a 14-game and an 11-game losing streak. Dayton Moore replaced Allard Baird as GM and began the housecleaning process that has been a work in progress. Mark Teahen had his best year to date and then (of course) messed up his shoulder, and we haven't seen that kind of power from him since.
38. 2005 (56-106, last place AL Central, 43.0 games back)
This was the worst team ever to wear a Royals uniform. Just looking at the roster makes me depressed. Zack Greinke (5-17, 5.80 ERA) or Runelvys Hernandez (8-14 5.59 ERA) might have had the worst season by a starting pitcher in Royals history if it weren't for Opening Day starter Jose Lima, who took every turn in the rotation despite a 5-16 record and a 6.99 ERA. Tony Pena quit... and they hired Buddy Bell. How could this year not be the worst ever?
39. 2004 (58-104, last place AL Central, 34.o games back)
I can't speak for all Royals fans, but I kept a healthy skepticism all throughout the '03 season, and when they faded out of contention, I shrugged and said, "It was fun while it lasted." But then something happened during the offseason. For some reason, I began to invent ways that they could contend in '04. And then when they came from behind on home runs by Mendy Lopez and a walk-off by Carlos Beltran, I believed again. The expectations we had for this team is what made 2004 the worst year ever. We expected them to be at least OK and we allowed ourselves to have hope for the playoffs. And then they went and sucked like they had never sucked before.
So there you have it, the Royals' seasons, ranked subjectively from 1-39. If you've been a Royals fan for a lot of years, I'd love to hear your opinions on the list.