Even my team - Leyton Orient - from two divisions below managed to beat Villa recently (evidence below if you find this had to believe)
Villa recently have been the epitome of mediocrity, the only reason to support them would be if you really wanted to experience the average football fan's mindset of frustration, boredom and impotent rage. They have spent most of the last 25 years playing undistinguished football, never good enough to excite the fans through success, but never bad enough to at least stir the passions by a close escape from relegation. Unless you feel some real sporting romance, or have some other association with Villa I would avoid them. Sport is supposed to stir emotion and Villa will just bore you to tears.
Liverpool are a much better choice if you want exciting football, great fans, amazing history (Villa's is quite rich to be fair, they have just not made much recently) and they are currently challenging for silverware, but not in a way which would make you seem like a glory hunter.
However you mention that you want to support an underdog. May I suggest you step outside the spoilt, wealthy environs of the 'Premier League' (Division One to anyone who understands that football didn't start when Murdoch opened his wallet in 1992) The PL is great if you want to watch teams of millionare mercenaries play football in muted stadiums filled with tourists and prawn sandwich munching corporate day-trippers, but you have to step down a division or two if you want to find the real soul of English football. English football is about long balls, centre-backs and centre forwards who look like builders, muddy pitches, proper tackling and crowds full of small children shouting abuse at players taking corner kicks.
More seriously, If you want a proper team - and a real underdog, you have, have, to look outside the premier league. The PL take the vast majority of the revenue which goes into English football, finances which before its inception in '92 used to be shared out much more equally between all 92 clubs. This has hugely imballanced the English game making it more and more difficult for teams outside the big three or four to challenge. It is now completely impossible to challenge for the title without a benefactor prepared to spend a serious fortune. There is no way teams from provincial towns like Derby or Nottingham, even Birmingham (the second city, where Villa are based) can win the league. Teams used to be able to come from the second division and be challenging for the title within a season or two. Leeds, Forrest, and Liverpool all managed this. No longer - you have to be established in the Champions League (another gated community within football) or have huge revenues to compete.
In a way that slightly contradicts my argument, this has had a big effect on the mid-ranking PL teams like Villa. Previously Villa could contemplate the possibility of making the occasional bids for glory. They won the league and European Cup in the early 80's but now they are comdemmed to season after season of mid-table nothingness, their only hope for excitement a cup run or perversely a tense battle against relegation. The moneyed elite have closed and locked the doors to the good times. In a way this makes them underdogs of a sort, but still ones who voted for the PL in the hope of greater monies but have been punished by their own greed.
Wow, didn't mean to rant on so much, it just came flooding out. In conclusion: for excitement support Liverpool, for boredom and self-hatred support Villa. For a clear conscience, quirky cool status, and excitement (we challenged all the way for promotion last season, only losing the play-off final at Wembley - all without spending a penny on a player since 2010) support Leyton Orient.
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