An interesting fact is that all the pubs in Newtown have operated on the same site since the last last century; although most have changed names, and one was closed for a while, that's still an impressive record. The downside to that is that apart from the re-opening of the Cricketers in 1999 as Kelly's, (replacing an unpopular McDonalds) no new pubs have opened in Newtown in more than 100 years. If you're ever downstairs and sober-ish at the Townie, take the time to check out the historical posters on the walls. The photo of the old swill-friendly bar in the Union in particular is a corker. I can also recommend this site and the Council's archive for some history.
A downside to preponderance of great pubs in Newtown is the dearth of decent bars; Madam Fling Flong being pretty much the only one. Let's hope Clover's new laws will eventually encourage the opening of some more bars in Newtown, enabling me to compose a Mayor's Top 5 Bars. In the meantime, here are the Mayor's Top 5 Newtown Pubs:
Honourable Mention - Nice Fac(ad)e, Shame About ...
The Sydney Park Hotel and The Union Hotel get an honourable mention for their classic Art Deco exteriors, but neither of them are really popular Newtown destinations. To be generous you could call Sydney Park Hotel tired - as the St Peter's end of King Street keeps picking up here's hoping that St Peters Hotel will start to attract a more varied clientele.

The Union Hotel has more character - at least in the front bar. For some reason the back bar was converted into a massive RSL style bistro a few years ago that has all the character of an airport departure lounge.
... and so to the Top 5.Number 5 Zanzibar

First entry in the Top 5 was a close one between Kelly's on King and ZanziBar. Both have improved noticeably in the last 6 months or so - Kelly's de-emphasising its Irishness (and seemingly running Karaoke 24/7 - how many times has the Mayor seen Fingers do Gay Bar ?), and ZanziBar de-emphasising the Moroccan theme that it inherited when it ceased being the Oxford.
ZanziBar just pipped Kelly's into the Top 5 for its more recent mini-renovation; downstairs now has an urban feel, complete with band posters and graffiti, and upstairs has become more of a club. Zanzibar also has Newtown's only rooftop bar which the perfect place for a gin tonic as the sun sets over King Street.
Number 4: The Sando

The Sandringham Hotel (known to all as the Sando) has been a mainstay of the Sydney live music scene for ages now. It seems to have finally survived the run in with the neighbours (who moved next to a pub that had been there for 100 years and started complaining about the noise - a pet hate of the Mayor's) and now reliably runs live music both downstairs (often free) as well as in the dedicated and sound-proofed gig area upstairs.
As well, it is rumoured that God has started drinking here since the Shakespeare changed its name. I'm pretty sure he'd be happy at how the Sando has maintained its unpretentious character over the years.
Number 3: Town Hall (The Townie)

Aptly known as the Downfall, anyone who's been in the Town Hall before midnight would justifiably be surprised by this placing. Horrifying by day, the Townie (of course) comes into its own after 11pm or so as the crowds drift in after gigs/shows or from other bars in the area. The Friday and Saturday night DJ sets add life to the downstairs crowd; upstairs, formerly the epicentre of late night townie life, is slightly calmer, and the smoking areas outside are always jammed.
Despite the size of the venue and the late hours it keeps, the vibe of the Townie is always chilled - non-judgemental, pretty much dick-head free, and friendly. The one downside of The Townie would have to be the bouncers, almost comically unable to detect the inebriation or otherwise of punters, and frequently and randomly restricting entry to completely sober patrons.

The Mayor was lucky enough to visit the manager's residence upstairs at the Townie a few years ago, and is very much hoping that one day the extensive outdoors area can be converted to Newtown's second rooftop bar.
Number 2: Coopers Hotel

Coopers Hotel, which started life as the Shakespeare in 1869, and was known for a while as the Cooper's Arms, has successfully survived a recent renovation managing to maintain the local feel of the downstairs bar while converting the upstairs backpackers into a sophisticated bar, bistro and outdoor dining/smoking area - even if the fishpond didn't last.
Like The Bank (name and location unchanged since 1880), the Coopers has become a destination bar, drawing outsiders to the various birthdays, engagement parties and the like upstairs on weekends. Recently live music has been re-introduced to the Coopers after a couple of years absence. Really the biggest problem with the Coopers these days is that it has to close at midnight.

Mayor's Number 1: The Courthouse Hotel

Perennial Newtown favourite and television star, Newtown's Courthouse aka 'The Courtie' has to be one of the best places in Sydney to while away a Sunny Sunday afternoon. The much loved beer garden has undergone a pretty serious tidy up recently that hasn't dimmed its popularity with jug drinking locals, and indoors has remained as grotty as ever. The pokies (such a key issue in 'Love is A Four Letter Word') are unobtrusive, and there's even a pinnies room. Being off the beaten track means that it draws a mostly local crowd, fiercely protective of the friendliest bar in Newtown.
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