At 22, Cusack had already become something of a teen icon for his leading roles in "The Sure Thing," "Better Off Dead," "One Crazy Summer," and "Hot Pursuit," and he wasn't interested in playing any more high schoolers -- until he read the part of Lloyd Dobler, aspiring kickboxer and professional romantic, in "Say Anything." Throughout the next decade and a half, Cusack continued to enjoy lead roles, usually as streetwise sharpies with a deep romantic streak, in such films as "The Grifters," "Bullets Over Broadway," "Grosse Pointe Blank," "Midnight in the Garden of Good and Evil," "Pushing Tin," "Being John Malkovich," "High Fidelity," "Serendipity,""Identity," and "Must Love Dogs." Over the past decade, Cusack has continued to star in mostly smaller-scale movies ("The Ice Harvest," "Martian Child," "War, Inc." and "The Raven"), though he did enjoy a smash with disaster movie "2012" and a modest hit with 2010's "Hot Tub Time Machine," a comedy that traded on nostalgia for his '80s glory days. He popped up last year as President Richard Nixon in "Lee Daniels' The Butler." At 47, he has several movies due over the next couple years, including David Cronenberg drama "Maps to the Stars" and biopic "Love & Mercy," in which he plays Beach Boys leader Brian Wilson.
Having made a splashy screen debut a couple years earlier in teen drama "River's Edge," 18-year-old Skye beat Jennifer Connelly for the "Say Anything" role of Diane Court, the beautiful but shy valedictorian courted by Lloyd. She went on to play memorable roles in "The Rachel Papers," "Gas Food Lodging," "Wayne's World," and "Four Rooms." The daughter of 1960s folk-rocker Donovan, she's been married twice, both times to pop stars: Beastie Boys rapper Adam Horovitz in the 1990s and Australian singer/songwriter Ben Lee since 2008. Now 43, she's due on screen again in the drama "Dear Eleanor," expected out later this year.
Character actor Mahoney had just worked with Cusack on "Eight Men Out" and convinced the younger actor to read the script for "Say Anything," for which the 48-year-old had already been cast as James Court, Diane's dad, who turns out not to be as heroic as she thinks. He continued to play character roles in such movies as "Barton Fink," "In the Line of Fire," "Reality Bites," "The American President," "Primal Fear," "She's the One," and "Dan in Real Life," but he became best known for playing salt-of-the-earth dad Martin Crane for 11 seasons on "Frasier." Now 73, he's a regular on TV's "Hot in Cleveland." Mahoney's last big screen role to date was in Rob Reiner's "Flipped" in 2010.
Taylor was 21 and coming off her first major film role, in 1988's "Mystic Pizza," when she got to play the "Say Anything" role of Corey, the leader of Lloyd's Greek chorus of platonic girlfriends, and the composer of 65 angry songs about her ex-boyfriend, Joe. She became one of the top indie-film actresses of the next two decades with leading and supporting roles in such films as "Short Cuts," "Rudy," "I Shot Andy Warhol," "Ransom," "The Haunting," "High Fidelity" (reuniting her with John Cusack), "Factotum," "Public Enemies," and 2013 horror hit "The Conjuring." On TV, she was best known for her recurring role as Lisa on "Six Feet Under." The 47-year-old is currently a series regular on Fox's "Almost Human."
Brooks (left) was 17 when she beat Julia Roberts (then best known for her "Mystic Pizza" role) for the role of D.C., one of Lloyd's platonic female friends, in "Say Anything." The movie's producer was her father, James L. Brooks, in whose "Broadcast News" she'd made her acting debut two years earlier. She went on to appear in her father's 1994 film "I'll Do Anything." After that, she quit acting and became a journalist and worked in TV production. Now 42, she was last seen in a 2007 episode of "E! True Hollywood Story" discussing her friend, Drew Barrymore.
Adlon made her acting debut at 15 in "Grease 2" (1982) but was primarily a TV actress before returning to film in "Say Anything" as Rebecca, one of Lloyd's platonic galpals. That same year, the 22-year-old embarked on what would be her primary career, as a cartoon voice actress, dubbing her distinctive raspy voice in the English-language version of Hayao Miyazaki's "Kiki's Delivery Service." Along with appearances in such live-action films as "The Adventures of Ford Fairlane," "Bed of Roses," and "Sgt. Bilko," Adlon lent her pipes to such animated series as "Bobby's World," "Teacher's Pet," Rugrats," "Recess," and current primetime series "Bob's Burgers." Most famously, she spent 13 years voicing Hank's son, Bobby Hill, on "King of the Hill," a role that won her an Emmy. In recent years, she's returned to more adult fare, such as Louis C.K.'s "Louie," which she co-produced and in which she played a recurring role as a character loosely based on herself. The 47-year-old has also co-starred in all seven seasons of "Californication," the last of which is about to premiere on Showtime.
Dean was 19 when he appeared in "Say Anything" as Joe, the ambivalent boyfriend who inspired Corey to write 65 songs. He went on to play the title role in 1992's gangster saga "Billy Bathgate," opposite Dustin Hoffman and Nicole Kidman. He played memorable supporting parts in "Apollo 13," "Mrs. Winterbourne," "Gattaca," and "Space Cowboys." In recent years, he's popped up a lot on TV, as a regular on "Bones," a guest star on "CSI: Crime Scene Investigation," and as a regular on cult-fave detective series "Terriers." Now 44, Dean last appeared on the big screen opposite Hilary Swank and Sam Rockwell in 2010's legal drama "Conviction."
"Say Anything" was actually the second of nine features that Piven, then 23, would star in with lifelong pal John Cusack. (The first was 1986's "One Crazy Summer.") After playing Lloyd's pal Mark, Piven would go on to appear with his friend in such films as "The Grifters," "Grosse Pointe Blank," and "Serendipity." On his own, Piven lent his loudmouth charm to "Say Anything" director Cameron Crowe's "Singles," as well as "Judgment Night," "PCU," "Heat," "Very Bad Things," "The Family Man," "Old School," "Smokin' Aces," and "The Goods: Live Hard, Sell Hard." On TV, he was a regular on "The Larry Sanders Show" and "Ellen" before landing his career-defining role as volcanic-tempered Hollywood agent Ari Gold on "Entourage" (2004-11). Now 48, Piven will be back on the big screen in "Sin City: A Dame to Kill For" in August and in the "Entourage" movie next year.
Fresh off her successes in "Broadcast News" (in which John Cusack had a cameo as an angry messenger) and "Working Girl," 26-year-old Cusack went without credit for playing sister to her real-life brother in "Say Anything." (In all, John and Joan have appeared in 10 movies together, most memorably, "Grosse Pointe Blank" and "High Fidelity.") In the 25 years since, Cusack has been a reliable comic actress in such films as "Addams Family Values," "In & Out" (for which she earned an Oscar nomination), "Runaway Bride," the "Toy Story" movies (she voiced Jessie the Cowgirl), and "School of Rock." For the past four years, she's co-starred on Showtime's "Shameless." Watch for the 51-year-old later this year on the big screen opposite Kristen Wiig in "Welcome to Me."
Stoltz, then 27, had starred in the movies "Mask" and "Some Kind of Wonderful," but he worked as a production assistant on "Say Anything" because he wanted to apprentice with director Cameron Crowe, whose films "Fast Times at Ridgemont High" and "The Wild Life" Stoltz had also acted in. "Say Anything" also saw Stoltz in a cameo as party host Vahlere. Stoltz went on to play cameos in Crowe's "Singles" and "Jerry Maguire," as well as enjoying starring roles in "The Waterdance," "Killing Zoe," "Sleep With Me," and "Mr. Jealousy," not to mention memorable supporting parts in "Pulp Fiction," "Little Women," "Rob Roy," and "2 Days in the Valley." In recent years, he's put to good use the skills he learned on the set of "Say Anything" as a director of episodic television, with recurring gigs on such shows as "Private Practice," "Glee," and "Nashville." The 52-year-old will next be seen on the big screen alongside Olivia Thirlby and Anton Yelchin in "5 to 7," a comedy debuting this month at the Tribeca Film Festival, with a possible wider release to follow.
Having written the scripts for teen flicks "Fast Times at Ridgemont High" and "The Wild Life," Crowe was commissioned by producer James L. Brooks to write a movie about a girl whose father turned out to be a criminal. That storyline became a subplot in "Say Anything," which marked the then 31-year-old's directing debut.. (He and his then-wife, Heart guitarist Nancy Wilson, have walk-on cameos in a scene at the mall.) After "Say Anything," Crowe went on to have another cult hit with "Singles" before scoring his biggest hit (and two Oscar nominations) for 1996's sports comedy "Jerry Maguire." In 2000, he won an Oscar for Best Original Screenplay for his autobiographical "Almost Famous." He stumbled with 2005 romance "Elizabethtown" but rebounded somewhat with 2011 family film "We Bought a Zoo." Now 56, he'll deliver his newest romance, starring Bradley Cooper and Emma Stone, this December.