Yoko Ono captured by threeASFOUR for Portrait of a Generation. Click here to view the slideshow.

Gaugin and van Gogh. Schnabel and Clemente. Warhol and Basquiat. Bacon and Freud. Prince and Sherman. Artists have been making portraits of each other throughout history. For the show Portrait of a Generation, which opens tonight at the Hole gallery in New York, owner Kathy Grayson asked 120 artists to create works. The exhibition is a counterpoint to nightlife impresario-graffiti artist André Saraiva's solo show, Andréopolis, also bowing here tonight. "André creates the spaces for people to come together and he's made this huge sculptural installation that's basically his dream of the city," says Grayson. "So for the main show in the space I thought it would be a nice compliment to give an image to the community in these places.” As such, she paired artists according to their significant others (Aurel Schmidt and Donald Cummings; Eric Yahnker and Allison Schulnik), those who hadn't previously known or worked with each other (Fab Five Freddy and Jeanette Hayes; Olivier Zahm and Wes Lang) and those whose pairing she knew would lead to explosive works (Kenny Scharf and Kembra Pfahler; Freeman/Lowe and Robert Lazzarini). Grayson is also planning to publish a "yearbook" catalog of the images, which goes on sale July 1. Until then, a few of the artists gave us a behind-the-scenes view on their respective pairings.

Aurel Schmidt and Donald Cummings
Two years ago, newlywed Aurel Schmidt rendered her then-boyfriend Donald Cummings, frontman of the Virgins, as the subject of her "Drug Voodoo Dolls" drawing series. His portrait was painstakingly comprised of an animated clonazepam prescription bottle torso, cigarette butt limbs, with pills for eyes and keys for feet. But her depiction of Cummings for this show was a bit more reactionary. "I did a self-portrait while I was crying because he hurt my feelings," says Schmidt of her crude image of herself titled "Love Me". She then rebuffed her hubby's overtures about painting her because she didn't want his work "taking away" from hers. "Donald is a professional model so it was easy for him to get into character. It only took five minutes and is totally stunning."

Eric Yahnker and Allison Schulnik
Painters Eric Yahnker and Allison Schulnik have been an item for 15 years, but the only portraits Yahnker had ever made of his girlfriend, he says, "were crude cartoons, typically involving penetration." He softened that image, a bit, in his portrait "Schulnik with Sticks". "For a long time, I've been telling people Ali was a Puerto Rican tranny," he jokes, "So I wanted to play on the 'chick with dicks' motif." Schulnik, in turn, made Yahnker into one of her hobo characters. "A lot of the paintings I make are probably portraits of Eric, or have some flavor of Eric," says Schulnik of the painting she made from a photo she took of him walking in a St. Louis park last year.

Yoko Ono and threeASFOUR
Adi Gil, Gabi Asfour and Angela Donhauser of threeASFOUR first met Yoko Ono in the fall of 2009 through her son, Sean Lennon, who invited the designers to a concert at his mother's studio. "When Kathy approached us with the idea [for this show] we thought it would be the perfect yin/yang match," says Gil, who manipulated a photo, now titled "One Two Three as Four", of Yoko taken by Sean Lennon and Charlotte Kemp Muhl. "We gave it our touch by applying our laser cut fractal shapes, then covered it with a transparent cut out plexi with a plexi mirror." In a photo by Pete Ross, Ono applied her words like tattoos ("Three as Fourever"; "Love"; "Peace") across the designers' bodies.