He gained worldwide media attention when he made a video detailing his attempt to visit all 171 Starbucks franchises in Manhattan in a single day during the summer of 2007.
He made headlines in January 2008 when he moved into an IKEA store in Paramus, New Jersey for a week as his apartment was fumigated.
In June 2009, Malkoff lived on an AirTran jet for 30 days in order to conquer his fear of flying. After completing this endeavor, he broke the Guinness World Record for most flights taken in a 30-day period with 135 flight segments.
On October 5, 2009 Malkoff traveled for four weeks in a Ford Fusion Hybrid around the country seeing how many U.S. mayors he could get to present him their key to the city. As of December 20, 2009, Malkoff has been presented 95 keys from mayors of cities that include Baltimore; Milwaukee; Tampa, Fla., Harrisburg, Pa.; Frederick, Md.; Durham, N.C.; Marietta, Ga.; and Fairfax, Va.
In February 2010 Malkoff made headlines again with a video in which to disprove the myth that New Yorkers are rude he was physically carried 9.4 miles in Manhattan by 155 individuals.
On January 20, 2010 Malkoff wrote a piece for Huffington Post entitled "The Will Ferrell Curse" which was featured by Nikki Finke on Deadline Hollywood. In it Malkoff discusses the fact that every time Will Ferrell has appeared as the first guest on a talk show the show has not made it past a season. Ferrell appeared as the first guest on The Tonight Show with Conan O'Brien, The Megan Mullally Show, and John McEnroe's talk show McEnroe which aired on CNBC.
In April 2011 Malkoff raced a crosstown Manhattan bus while riding a Big Wheel tricycle to point out how slow the buses in New York are.
In July 2011, Malkoff tried to get thrown out of a Manhattan Apple Store with stunts that included having a pizza delivered, bringing in a band to play live music, bringing in a pet goat, and trying to have a quiet candlelit dinner with his wife.
In August 2011, Malkoff launched 101 other things to do in Holland, besides the smoking of weed, including descend the Euromast (328 feet) in Rotterdam, try to pay off the U.S. debt by collecting money in the Vondelpark in Amsterdam and fool around with street performers at the Dam square in Amsterdam.
On September 29, 2011, Malkoff gave free cab rides out in New York with the catch of strange behavior and other quirks from the driver, as well as antics as the passenger area slowly filling with popcorn.
In April 2012, Malkoff tested the limits of Netflix by watching as many movies as he could in one month. During the month, he watched 252 movies from opening to ending credits. For being the heaviest Netflix user that month, Malkoff was invited to Netflix Headquarters where he met Reed Hastings, CEO of Netflix.
In August 2013, Malkoff used Skype to video chat with residents of 162 countries, including North Korea.
Malkoff currently makes videos for the comedy website My Damn Channel and has hosted the Carson Podcast for more than three years, a single-microphone audio interview series in which he examines the career of talk show host Johnny Carson by interviewing employees and guests of The Tonight Show Starring Johnny Carson, an NBC-TV television program broadcast from 1962 to 1992.