Drug arrest? Check. Rehab? Check. Probation violation? Check. Jail time? Check.

With a speed and ease that Hollywood insiders are calling “astonishing” and “record-setting,” Lindsay Lohan has been dutifully checking off items on her own celebrity bad-girl to-do list, or “bucket list.”

A bucket list is a list of goals a person hopes to accomplish before he dies, or “kicks the bucket.” The phrase was popularized by a trite and predictable movie starring Fred Sandford Morgan Freeman and Jack Nicholas.

Lindsay Lohan, seen after crossing off number 23 of her bucket list: "Fall into drug-induced coma from injecting Tidy Bowl cleaner."

According to Lohan’s latest love interest, Ginnie “Big Hands” Mahoney, a prison guard Lohan met during her brief stint at the Los Angeles County Jail, the overexposed under-talented media phenom created her list of depravity-based “before I die” goals soon after filming the 2003 surprise hit remake of Freaky Friday.

“She was at one of them cast parties  just after they finished making the picture. Her mom and dad were there hoggin’ all the attention, and she vowed that she would never let that happen again,” said Mahoney, her gel-spiked hairdo glistening in the fluorescent lighting of the prison cafeteria. “And that’s when her Bucket List was born. Still, I think she’ll tell ya her parents have put up quite a competition. I doubt she’d call herself the winner yet.”

“She really has gone full throttle,” said TMZ contributor Ralph Harrison. “She takes it all very seriously. When it comes to celebrity neurosis and fame-induced stupidity, this trollop is the consummate professional. Plus, she has an ‘ew’ factor that I think no other celebrity can touch.”

When asked if he could recall a swifter transition from fame to infamy, Harrison said “Courtney Love I guess comes to mind. But she was a skank to start with so the trip was short. I think the key for LiLo is that she got started early, set goals for herself, and she wouldn’t let anything distract her – not friends, not counseling, not common sense.

“You see, Courtney and Brit seem to haphazardly fall into turmoil; like they were just too dumb to avoid it. Lindsay has clearly been more calculating, always encountering celebrity misadventure at exactly the right moment, and in exactly the right context. With her, you can tell it’s no accident. She is a master of her craft.”

Lohan admits, however, that her list is far from fulfilled. “Well, like, I really feel like I’ve made some progress, and I’m proud of what I’ve accomplished,” said the former child star moments after sprawling face-first to the curb as she exited the passenger seat of her attorney’s Mercedes, “but I still have a long way to go. For instance, a sex tape still eludes me. No one feels comfortable producing video evidence of their sexual encounters with me. Guys, girls, doesn’t seem to matter. Not sure why, although one said I look ‘splotchy’ on video. Plus, I’m usually too wasted to remember to set up the camera.”

Lohan did state, however, that number 18 on her list was her recent demand for an apology from the court that sentenced her for violating her probation. “No one, not even a degenerate celebrity, has ever been so smug, so obnoxious, so unspeakably dense. Until me! Whoohoo! Run and tell that, Montana Fishburn! B**** thinks she can go toe to toe with me? Bring it on!”

A W&E Exclusive! A page from Lohan's bucket list

Asked if she would reveal any yet-to-be-crossed-off milestones on her Bucket List, Lohan played coy. “Well, let’s just say one of my most favorites involves RuPaul, live television, and ultimately a complaint from PETA.” Asked to clarify if there was something on her list that would come as a surprise, Lohan tried to respond, but instead orally disgorged a fetid cocktail of gin and Reese’s peanut butter cups on this reporter’s Nikes, effectively ending the interview.

Harrison says he respects what LiLo has pulled off so far, but it is left to be seen how she matches up with other dysfunctional celebrities, many of whom have set the gold standard for Hollywood misbehavior.

“Well, you’ve got the Sheens and the Robert Downeys to factor in; there’s the Whitneys and the Gibsons. We’re talking about celebrity twits who not only crashed at a high level, but who have also had amazing staying power … they won’t leave the stage – or die – no matter what they did or what they put their bodies through. So while you have to admire Lohan’s accomplishments so far – the broad does have game – whether she earns the title of most miserable and pathetic celebrity nitwit of all time is still an open question. Only time will tell.”

[Editors note: Despite the woman’s multiple, multiple requests, harassing phone messages and death threats, W&E has declined to interview Lindsay’s mom, Dina, for this story.]