Siff was born in Brooklyn, New York. He creates images that blend Pop Art and Abstract-expressionism. His distinct handmade style merges elements of abstraction, street, and fine art while his work embodies emotionalism normally absent in urban art.
Siff's first exhibition, "the heartfirebreathemanifesto" was hosted at the Standard Hotel in Hollywood on February 13, 2006 with all proceeds from this exhibit donated to J.U.i.C.E. (Justice By Uniting in Creative Energy). Since 2006 Siff has exhibited all over the world including Los Angeles, New York, London, Italy, Dublin, and Vancouver.
Siff has done commissions and installations for Deitch Projects, The Standard Hotel, Mercedes Benz, Tumblr, Christie's, Sotheby's, Vans, Red Bull, The Art of Elysium, Siren Studios, Wexlers Deli, and Warner Bros. Records among others. In addition, Siff has collaborated with artists RISK, James Georgopoulos, 2wenty and Beau Dunn. His work has been seen in publications such as Interview, Treats Magazine, The Wall Street Journal, LA Times, Complex, and LA Weekly.
In Spring 2013, Siff was selected by Vans Custom Culture to be one of their "Art Ambassadors", inspiring students across the United States to embrace their creativity. His hand-painted custom Vans sneakers were on view at The Whitney Museum of American Art in New York City. Siff's work can be seen at ACE Museum in Los Angeles where he painted a mural for a charity art auction held by renowned auction house, Christie's and non-profit, The Art of Elysium.
In October 2013 Siff collaborated with Helmut Lang and Project Angel Food, a Los Angeles-based charity whose mission is to help those affected by HIV/AIDS, Cancer, Diabetes, and other life-threatening diseases. In this collaboration he hand painted 21 limited edition, one of a kind Helmut Lang tees. "The line work, characters, and poetry aimed to nourish the body and spirit, just as Project Angel Food does with their mission," said Siff. The private event was held on October 17 at Helmut Lang's flagship store on Melrose Avenue in West Hollywood, CA. All 21 tees were sold out and 100% of the proceeds from the sale of these original works benefited Project Angel Food.
In April 2014, the Santa Monica Museum of Art showcased a recreation of Siff's downtown Los Angeles art studio where he painted 50 portraits of the homeless youth he encountered while spending a day at the Safe Place For Youth for the Face 2 Face Fundraising Gala.
Also in April 2014, Siff exhibited in the Santa Monica Museum of Art's Precognito/Incognito 10 alongside work from Ed Ruscha, John Baldessari, Sage Vaughn and Oscar Murillo.
In June 2014, Siff's work was included in The Museum of Modern Art PS1 exhibition Rockaway! to celebrate the ongoing post-Superstorm Sandy Recovery. Curated by MoMA PS1's director Klaus Biesenbach, in close collaboration with Patti Smith, Rockaway Beach Surf Club, the Honolulu Biennal, and the Rockaway Artist Alliance, this group show included the "Experience Rooms," Siff painted in the Rockaway Beach Surf Club bathrooms. Other artists in the exhibition included, Marina Abramovic, Patti Smith, Janet Cardiff, Brandon D'Leo, James Franco, Michael Stipe, Tom Sachs, and Adrián Villar Rojas.
As an actor, Siff started out on stage at the New York City Opera at Lincoln Center. Among the operas he sang in were; Carmen, Tosca, Lucia, and Turandot. He has been cast in the dual role of Barry Williams/Greg Brady in Fox's True-Life story of, The Brady Bunch: The Final Days. In I.F.C.'s Rome & Jewel, a modern update of William Shakespeare's Romeo and Juliet, he played the role of Tybalt. He has also guest starred on Showtime's Nurse Jackie, HBO's, How to Make It in America, and C.S.I.: NY.
In 2008, Siff wrote and starred in, The Nothing Boys, a critically acclaimed semi-autobiographical play about a young man who returns home to his high school for his 10-year reunion only to find one other student in attendance. The Nothing Boys was produced by Rob Weiss, best known as producer of HBO's Entourage. The play ran from May 2 through July 27 in Hollywood's Theater District. A portion of the proceeds from, The Nothing Boys was donated to Covenant House California.
In Spring 2010, Siff's experimental art short film, Sequential Paint, written and directed by Stephen Dackson, was a featured selection at the NewFilmmakers Series in New York City's Anthology Film Archives. The film also screened at various exhibits, art shows and galleries in Los Angeles, including the opener of the 2006 Santa Ana Film Festival.
As a voice actor Siff appears in the video game series, Grand Theft Auto as the voice and body of Rocco Pelosi. Rocco Pelosi is featured in Grand Theft Auto IV: The Ballad of Gay Tony (2009) and Grand Theft Auto V (2013).