Once upon a time I had a really well-considered evaluation of the top Badger teams of all time. '62 was near if not the top. But they lost to #1 USC in the Rose Bowl. Ouch. I think the '99 team was better than the '98 team, record notwithstanding, and I think both may have been better than '93. Tough call. Of the more recent teams, '06 (Bielema's 1-loss team) was good, but not
that good. The 2010 and 2011 teams are the hardest for me to swallow, but mostly because they didn't win their Rose Bowls, but should have (to be fair, Oregon and TCU were really good, too--I'm sure their fans would dispute the "should have" comment).
In 2010, the Tolzein-as-a-senior led Badgers lost to a very good (11-2) Michigan State team in East Lansing in a game that I still remember being brutal to watch. I think that was the game Bielema was penalized in, costing the team momentum and a chance, but maybe I'm just looking for something to pin on him. The Badgers shouldn't have lost to TCU in the Rose Bowl, and had a chance to tie it in the end, but failed. TCU was good, but Chryst (the OC at the time) tried to get too cute, rather than just running the much bigger Badger offense straight into TCU's middle. Once the Badgers did that, they started their ultimately *just short* comeback (not unlike 1962 vs. USC).
2011 was that one glorious year with Russell Wilson. The football gods shined on Madison when Wilson decided to go there, but took their vengeance in each of the three losses. In two, at Michigan State and at Ohio State, the Badgers gave up hail Marys to lose on (effectively) the game's final play (Ohio State's was with 20 second left, but whatever). Each is still painful to this day. At least Michigan State was a good team. Ohio State wasn't even good that year, and that stupid bomb on a broken play beat us (that "us" is just for Badge

). And then the loss to Oregon in the Rose Bowl in a game that basically had no defense (actually it had some, but not enough). Jared Abbredaris, who was as sure handed as WRs come, fumbled the ball as he was going out of bounds late in the 4th quarter and the ball inexplicably stuck like velcro to the grass instead of following the momentum out of bounds. The ball bounces funny, except when it doesn't bounce, which was *funny.* The Badgers still had a chance to come back from one score down when Wilson made a mistake in clock management and the Badgers ran out of time.
Maybe it's that shiny offenses are easier to appreciate than fantastic defenses, but that 2011 team felt like it could have beaten anyone...except that three times it didn't. Seems funny to rate a 10-3 team so highly among the great Wisconsin teams, but Russell Wilson, Montee Ball, James White, Chris Borland, Peter Konz, Kevin Zeitler, Aaron Henry... they were good.
This year's team deserves a mention--and we'll see what they do in the Orange Bowl. If I had to pick a team that at it's peak was the best, I would choose between 2011 and 1999 (once Bollinger became the starter), and probably give the nod to '99, but not without hedging a lot.
'99 had Bollinger under center, Dayne with Bennett as his backup, Tauscher and McIntosh on the line, and Wendell Bryant, Doering, Echols, and Fletcher on defense. That was a really good team.
Honorable mention for what could have been: in 2008 the team really, really talented (except for at QB), and it stunk, 7-6 with a blowout loss to Florida State in the Outback Bowl. Chemistry and leadership matter.