It’s that time of year again, faithful gossip devotees. All Hallow’s Eve, the favored holiday for anyone hoping to channel his or her inner bimbo, is just around the corner. While a sizable female majority will continue to capitalize on the “slutty bunny / slutty cop / slutty prostitute” costume bracket, this Halloween is also likely be dotted with innumerable references to The Summer of Celebrity Death.

Just as the late Heath Ledger’s Joker dominated 2008’s festivities, expect to see an overabundance of silver-gloved Michael Jackson impersonators moonwalking their way to the next kegger this Saturday. The late infomercial king Billy Mays’s family has already learned to embrace the cultural obsession with commemorating celebrity death. Mays’s son is offering a prize to the three best costumes immortalizing his father. In order to properly pay homage to the late Mays, the prize better include a tub of OxiClean mixed with an eight-ball of high-grade Colombian blow.

Speaking of snowy weather, let’s check in with Hollywood’s A-list trainwreck Lindsay Lohan. Try as I might to write a single column neglecting to mention Miss CokePants, the sometimes actress and failed fashion designer continuously manages to generate highly unflattering but entertaining press about herself.

This week, LiLo’s father Michael Lohan — a man better known for his repeated jail stints and his recent friendship with Dad of the Year Jon Gosselin — has reached out to his estranged daughter in the best way possible: by going on Maury to beg his little girl to quit the drugs and get her life straightened out. Oh yeah, and to maybe cut him another check — things have been a little tight lately with the recession and all that. At least the man refrained from commenting on Lindsay’s unmentionables, unlike Papa Winehouse, who proudly announced to the world that daughter Amy — and her recently enhanced silicone breasts — is just fine.

Poor little LiLo reacted to unanimous worldwide ridicule of her Ungaro fashion line by going on a month-long bender, passing out in nightclubs and causing the weekly tabloids to speculate that the end is near for hapless Lindz. Luckily, her 15-year-old sister Ali — you know, the one who briefly had an E! reality show showcasing Dina Lohan’s attempts to turn her youngest daughter into a cash cow — is in tow for the festivities, joining her big sister for vodka-Red Bull flavored nights on the L.A. nightclub circuit. At least if Lindsay’s health doesn’t hold out, there will be another little Lohan trainwreck to follow.

One person who won’t be frequenting the club scene for much longer is rapper Lil Wayne, who recently pled guilty to second-degree gun possession and will likely be sentenced to a year in the pokey. Why exactly would a millionaire recording artist, whose claim to fame is comparing Blow Pops to oral sex, need to pack heat on his tour bus? Apparently he had to keep those crazed fans in check. He’s the second high-profile hip-hop artist convicted of felony gun charges this year, effectively stealing T.I.’s thunder. Hopefully the two will bond behind bars and release a mixtape titled “Whatever You Like a Lollipop.” Martha Stewart will grace the cover art and Plaxico Burress is expected to guest.

Shifting from the very real shackles of prison to the metaphorical shackles of parenthood, a slew of reality starlets are set to give birth in the coming weeks. Thank god; I was getting sick of relying solely on the Gosselins for my weekly dosage of televised child exploitation. Former “Girls Next Door” Playboy groupie Kendra Wilkinson has taken a break from hawking her dumb-blonde schtick and is showing off her expanding belly for a variety of celebrity weeklies. Thankfully she’s expecting a boy, so the child will be groomed for football tournaments rather than magazine centerfolds.

Kourtney Kardashian — the one who didn’t just put together a hasty wedding and hasn’t leaked a sex tape yet — is also with child. She reportedly became preggers after a series of unprotected flings with her cheating ex-fiancé Scott Disick, who has now been upgraded to temporary boyfriend. The entire pregnancy, from the early “Oh-shit-I-missed-my-period” stages all the way to the tenuous “Should-I-get-an-abortion?” debates, has been captured by a live camera crew for Kourtney’s latest E! reality show. These tapes will be a lovely supplement to future “How You Were Born” conversations between Kourtney and her Little Kardashian. Let’s just hope the TV crew doesn’t capture the live birth for a raw two-hour special.

Speaking of out-of-touch reality starlets, aspiring singer Heidi Montag recently dissed her own sister by refusing to attend her birthday party. Heidi allegedly opted out of the festivities because wasn’t going to be paid for the appearance. The fact that anyone would pay Heidi to stare at a camera for 23 minutes every week, much less attend an actual publicized event, is enough to make even the most upbeat person lose all faith in humanity.

Heidi’s sister-in-law and “Hills” co-star Stephanie Pratt is also fighting her own battle to maintain media relevance. The reality star was recently arrested in Hollywood for suspicion of driving under the influence. To her credit, Stephanie is related to Spencer Pratt, and if I had to deal with his fame-whoring ways every day I’d be pounding the vodka harder than Paula Abdul.

If you’ve been feeling like there has been something intangible missing from your life these past three weeks, there’s a likely answer. Disney pop-tart Miley Cyrus recently quit Twitter, unceremoniously dumping the 2 million-plus followers she had accumulated. Apparently little Miley’s newest boyfriend didn’t like that she was documenting her every burp for a gaggle of fans. I’m sure Daddy Billy Ray and the Disney execs had absolutely no interest in preventing yet another leak of a scantily-clad, mildly racist photo.

What will the Twitteratti do now that Hannah Montana isn’t tweeting all her profound thoughts for the masses? Are they really expected to follow Audrina freaking Patridge?

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