Yep, it can actually work. Source: Supplied

David Phillips was a civil engineer who taught at the University of California. Now, most people know him as ‘the pudding guy’.

In 1999, Mr Phillips gained notoriety for successfully exploiting a Healthy Choice pudding promotion. Pudding, as in pudding cups — those nondescript gelatinous desserts Americans love so much.

The Healthy Choice promotion was one of those mail-in deals in which you sent in proof-of-purchase to get something in return. In this case, for every 10 bar codes, the redeemer would get 500 frequent flyer miles in return. Mr Phillips calculated that the miles were worth way more than the cost of the food.

He found that individual pudding cups, at 25c each, were the cheapest of the Healthy Choice range and that if he sent in those labels during May 1999 (when there was a double points special), he could get 1000 miles for every $2.50 he spent.

David Phillips with his family, who are still flying around the world for free. Source: Getty Images

He bought up all the pudding he could get his hands on (telling everyone he was stocking up for Y2K — yeah, remember that?) and spent just over $US3000 all up. In return, he got 1.25 million miles, worth about $US150,000. So the return on his venture was $50 for $1 spent.

To help peel off all the promo stickers on time, he enlisted the local Salvation Army and told them that if they helped him, he will donate all the pudding to the charity. He also managed to get an $US800 tax deduction for his generous ways. Nicely done.

Director P.T. Anderson even included Mr Phillips’ exploits as a subplot in his 2002 film, Punch Drunk Love.

Adam Sandler in Punch Love Drunk, amassing loads and loads of pudding. Source: Supplied

THE PRETENDER

Leonardo DiCaprio made Frank Abagnale Jr famous in Steven Spielberg’s Catch Me If You Can. The movie version of Abagnale was a troubled young guy who, blessed with intelligence and charm, posed his way through a number of positions including as a doctor, a pilot and a lawyer.

The real-life version got away with pretty much the same adventures, for a time. He also impersonated a doctor, a lawyer and an airline pilot.

He stepped into pilot shoes by calling Pan Am’s uniform distributors and told them he had lost his threads, using a fake employee ID to ‘verify’ his legitimacy. A master forger, he also dummied up a pilot’s licence. While he was never behind the wheel of a plane in motion, it was estimated that he flew over 1.6 million kilometres to 26 countries by ‘deadheading’ (when crew fly for free).

Frank Abagnale (second from the left) with his Hollywood double. Source: AAP

He also faked being a doctor by conning his way into a job as a supervisor to interns, which required to real medical work on his part. He also forged a Harvard law transcript and passed the Louisiana state bar exam at 19 but resigned his legal job after nine months once colleague started to make inquiries into his background.

But all that fun aside, where Abagnale really made his cash was check forgery. Of course, it was more rudimentary in those days and a little precision and a good printing machine pretty much got the job done.

By his own estimates, Abagnale passed $2.5 million worth of forged or bad checks over five years, which was a lot of money in the 1960s. One trick he said he pulled was to print his personal bank account number on a stack of bank deposit slips and then slip them behind the uncompromised ones. So when a customer went to deposit their cash, they would inadvertently put their money into Abagnale’s account.

Frank Abagnale now makes a mint consulting for law enforcement and banks. Source: AAP

But the law did catch up with Abagnale. He was caught by the time he was 21 but served less than five years in various prisons.

After his release, he convinced banks that with his knowledge, experience and wiles, he could show them how to protect themselves from people like him. He made $500 from his first consulting gig but was getting paid upwards of $15,000 for lectures in the 2000s. He’s consulted to clients including Target, banks, insurance companies and the FBI.

He’s now married with three kids.