Trivia: Over the course of a single decade - the 1990s - Leonardo DiCaprio graduated from supporting work in television to a status as one of the most sought-after Hollywood actors under 30. After leading roles in William Shakespeare's Romeo + Juliet and James Cameron's Titanic, the actor became a phenomenon, spawning legions of websites and an entire industry built around his name. DiCaprio was born November 11, 1974, in Hollywood, CA. The son of a German immigrant mother and an underground comic book artist father who separated shortly after Leonardo's birth, he was raised by both of his parents, who encouraged his early interest in acting. At the age of two and a half, the fledgling performer had his first brush with notoriety and workplace ethics when he was kicked off the set of Romper Room for what the show's network deemed "uncontrollable behavior." After this rather inauspicious start to his career, DiCaprio began to hone his skills with summer courses in performance art while he was in elementary school. He also joined The Mud People, an avant-garde theater group, with which he performed in Los Angeles. In high school, DiCaprio acted in his first real play and began doing commercials, educational films, and the occasional stint on the Saturday morning show The New Lassie. In 1990, after securing his first full-time agent at the age of 15, DiCaprio landed a role as a teenage alcoholic on the daytime drama Santa Barbara. He also continued to appear on other TV shows, such as The Outsiders and Parenthood, and made his film debut in the 1991 horror film Critters 3. The actor got the first of many big breaks with a recurring role on the weekly sitcom Growing Pains. His portrayal of a homeless boy won him sufficient notice to get him an audition for Michael Caton-Jones's harrowing screen adaptation of Tobias Wolff's This Boy's Life. DiCaprio won the film's title role after beating out 400 other young actors and it became his career breakthrough. The 1993 film, and DiCaprio's performance opposite Robert DeNiro, won raves and the actor further increased the adulation surrounding him when, later that year, he played Johnny Depp's mentally retarded younger brother in Lasse Hallström's What's Eating Gilbert Grape. DiCaprio won an Oscar nomination for Best Supporting Actor for his performance, and at the tender age of 19, was hailed as an actor to watch. Subsequent roles in three 1995 films, Sam Raimi's Western The Quick and the Dead; Total Eclipse (as the bisexual poet Rimbaud) and The Basketball Diaries (as a struggling junkie) all put the actor in the limelight, but it wasn't until the following year that he became a bona fide star, thanks to his portrayal of Romeo opposite Claire Danes in director Baz Luhrmann's William Shakespeare's Romeo + Juliet (1996). The success of the film brought DiCaprio international fame, many lucrative opportunities, and frequent comparisons to predecessors such as James Dean. After starring with Diane Keaton, Meryl Streep, and DeNiro in Marvin's Room (1996), DiCaprio achieved iconic status with his starring role in James Cameron's Titanic. With Kate Winslet as the female lead, the film became a box office sensation, earning garnered 14 Oscar nominations, winning 11, including Best Picture and Best Director, and earned a whopping 1.8 billion dollars at the global box office. DiCaprio's much-discussed exclusion from the Oscar nominations did nothing to hurt his popularity, and somewhat ironically, he next chose to parody his own celebrity with an appearance in Woody Allen's Celebrity (1998) as a badly behaved movie star. After displaying his nastier side, he tackled a dual role as twins in the same year's swashbuckler The Man in the Iron Mask, opposite Jeremy Irons, Gabriel Byrne, John Malkovich, and Gérard Depardieu. Following the commercial success of the film, DiCaprio then traveled in a completely different direction, with a lead role in Danny Boyle's screen adaptation of Alex Garland's novel The Beach. The film met with eager anticipation from its first day of shooting, as Leo fans everywhere waited with baited breath to see what kind of impression their golden child would next make on the film world; unfortunately, the muddled Beach drew neither praise nor box-office success. In 2002, DiCaprio began what became a series of collaborations with the legendary director Martin Scorsese, starting with the the epic Gangs of New York (2002) - a sprawling tale of gangland violence in early America. Reportedly delayed by a year given much-publicized disagreements between director Scorsese and producer Harvey Weinstein, the film was ultimately released in time for the 2002 holiday/Oscar season. The tireless actor re-united with director Steven Spielberg with the release of Catch Me if You Can, the true-life tale of Frank Abagnale, Jr., a scam artist so effective that he eluded authorities while assuming a number of high-profile false identities and racking-up over $2.5 million in fraudulent checks. Two years later, DiCaprio and Scorsese embarked on a sophomore collaboration - the biopic The Aviator (2004), with DiCaprio in a critically-praised, star-making turn as eccentric billionaire genius Howard Hughes in The Aviator. DiCaprio and Scorsese scaled even greater heights in 2006 with The Departed, a crime drama in which DiCaprio played an undercover cop trying to bring down criminal Jack Nicholson. Doubling up during Oscar season yet again, that same year he played the lead in Edward Zwick's Blood Diamond, as an Afrikaner who must team up with a South African mercenary in order to find a rare gem of great value to both of them. Both films opened to praise and box-office success, resulting in dual Golden Globe nominations. Perhaps pushing its luck, Warner Bros. -- the studio behind both films -- campaigned DiCaprio for a lead Oscar in Diamond and a supporting one in Departed; Oscar voters only nominated him for Diamond. In the years that followed, DiCaprio showed no signs of tapering off when it came to challenging and even iconic roles. He joined Titanic co-star Kate Winslet, megaproducer Scott Rudin and others for the blistering marriage drama Revolutionary Road (2008), teamed with Scorsese a fourth time for the thriller Shutter Island (2010), toplined Christopher Nolan's complex, elusive sci-fi drama Inception (2010), and in 2011, worked with director Clint Eastwood and screenwriter Dustin Lance Black on the biopic J. Edgar (2011), playing the famous titular FBI director. Meanwhile, DiCaprio also signed on for another collaboration with Baz Luhrmann - a new adaptation of F. Scott Fitzgerald's The Great Gatsby, co-starring Tobey Maguire and Carey Mulligan, not to mention a first-time collaboration with Quinten Tarantino for Django Unchained. In 2013, he and Scorsese joined forces yet again for The Wolf of Wall Street, earning DiCaprio two Oscar nominations, for both Best Actor and Picture.DiCaprio took the next two years off, focusing on environmental causes, but came back in 2015 in Alejandro G. Iñárritu's The Revenant. He nabbed his sixth Oscar nom for the film and finally landed his first win, for Best Actor.The hybrid-car driving DiCaprio has also been an outspoken proponent of environmentalism, a topic he is so passionate about he was allowed to interview then-President Bill Clinton on the issue in a 2000 televised prime-time special.

Trivia: Long the bad boy of Hollywood, Sean Penn is also among the most fiercely talented actors of his generation. He was born August 17, 1960, in Burbank, CA, the second son of actress Eileen Ryan and director Leo Penn. He grew up in Santa Monica, in a neighborhood populated by future celebrities Charlie Sheen and Emilio Estevez, the sons of actor Martin Sheen. Penn's older brother, Michael, is a singer/songwriter-turned- director, while younger sibling Chris is a noted character actor. The children spent much of their free time together, making a number of amateur films shot with Super-8 cameras. Still, Penn's original intention was to attend law school, although he ultimately skipped college to join the Los Angeles Repertory Theater. After making his professional debut on an episode of television's Barnaby Jones, he relocated to New York, where he soon appeared in the play Heartland. A TV-movie, The Killing of Randy Webster, followed in 1981 before he made his feature debut later that same year in Taps.Penn shot to stardom with 1982's Fast Times at Ridgemont High; as the stoned surfer dude Jeff Spicoli, he stole every scene in which he appeared, helping to elevate the picture into a classic of the teen comedy genre; however, the quirkiness which would define his career quickly surfaced as he turned down any number of Spicoli-like roles to star in the 1983 drama Bad Boys, followed a year later by the Louis Malle caper comedy Crackers and the period romance Racing With the Moon. While none of the pictures performed well at the box office, critics consistently praised Penn's depth as an actor. A turn as a drug addict turned government spy in John Schlesinger's 1985 political thriller The Falcon and the Snowman earned some of his best notices to date, but Penn's performance was quickly lost in the glare of the media attention surrounding his very public romance with pop singer Madonna, which culminated in the couple's 1985 media-circus wedding.While Madonna actively courted press attention, the private Penn made his loathing for the media quite clear; his run-ins with the paparazzi quickly became the stuff of legend, and the notoriety of his temper began to eclipse even his immense acting ability. His penchant for fisticuffs, combined with other civil infractions, ultimately resulted in a 30-day jail sentence; more seriously, his marriage to Madonna began to buckle under the weight of media scrutiny, and, as the couple's star collaboration in the 1987 movie Shanghai Surprise met with box-office disaster, their private relationship was also over. Soured by the Hollywood experience, Penn did not resurface prior to 1988's Colors, which proved to be his biggest hit in some time. He next appeared in Brian DePalma's Vietnam tale Casualties of War, followed by a turn opposite his idol, Robert De Niro, in the 1989 comedy We're No Angels.After starring in the gangster melodrama State of Grace, Penn wrote and directed 1991's The Indian Runner, a film inspired by a Bruce Springsteen song and shaped in the image of the films of John Cassavetes. After an almost unrecognizable turn as a troubled attorney in the 1993 DePalma thriller Carlito's Way, Penn announced his intention to retire from acting in order to focus his full attentions on directing; however, after helming 1995's The Crossing Guard with Jack Nicholson and Anjelica Huston, he was back onscreen, winning an Academy Award nomination for his gut-wrenching portrayal of a death-row inmate in Tim Robbins' Dead Man Walking. By 1997, Penn's wishes for retirement were but a memory as he enjoyed his busiest year yet: In addition to starring opposite second wife Robin Wright in Nick Cassavetes' She's So Lovely -- roles which won both spouses acting honors at the Cannes Film Festival -- he also appeared in the David Fincher thriller The Game and in Oliver Stone's U-Turn. He found further acclaim the following year for his roles in the adaptation of David Rabe's Hurlyburly and Terrence Malick's The Thin Red Line. In 1999, he had a cameo appearance in Spike Jonze's Being John Malkovich and earned his second Oscar nomination as a callous '30s jazz guitarist in Woody Allen's Sweet and Lowdown, while 2000s adaptation of Anita Shreve's novel, The Weight of Water, starred Penn as a poet embroiled in a small town murder mystery. In 2001, Penn would play a fame-craving impressionist in The Beaver Trilogy, serve as narrator in director Stacy Peralta's skateboarding documentary Dogtown and Z-Boys, and direct the psychological drama The Pledge, which marked Penn's second collaboration with Jack Nicholson. In 2002, Penn would once again win critical praise with his Oscar-nominated portrayal of a developmentally disabled man struggling to retain custody of his daughter in I Am Sam.After the 2001 terrorist attacks on the World Trade Center and Pentagon, the left-leaning actor's outspoken political views garnered a great deal of attention from right-wing pundits, including the much aggrieved Bill O'Reilly, who found himself on the receiving end of Penn's animosity in a controversial interview with Talk magazine. Though O'Reilly demanded his viewers boycott any of Penn's future films, it appears his career has remained relatively unscathed. In 2002, Penn directed a segment for the French-produced 9'11"01, which was met with mixed reviews, while his participation in Burkowski: Born Into This (2002) helped the film win a nomination for the Grand Jury Prize at the 2003 Sundance Film Festival. The year 2003 was, in fact, an eventful year for Penn; he participated in two small but nonetheless critically acclaimed films -- Michael Almereyda's documentary This So-Called Disaster and Alejandro González Iñárritu's low-key urban drama 21 Grams -- while managing to claim yet another Hollywood success in actor/director Clint Eastwood's highly lauded Mystic River. In 2004, it was this third film that garnered Penn his fourth Academy Award nomination and, ultimately, his first win. The Oscar, coupled with a standing ovation by the audience, showed once and for all that Penn's unorthodox approach to his acting career hadn't had an adverse effect on his popularity.The following year Penn would return to the screen to document one man's chilling descent into madness in the fact-based psychological drama The Assassination of Richard Nixon, but despite generally favorable reaction from critics the grim feature failed to make much of an impression at the box office. Subsequently sticking to politics with Sydney Pollock's 2005 thriller The Interpreter, Penn would this time find his character attempting to prevent the assassination of a high profile political leader rather than personally carry one out. By the time Penn essayed the role of a populist Southern politician modeled loosely on Depression-era Louisiana governor Huey Long, it seemed as if the serious-minded actor's career had finally become as political as the boat-rocking rhetoric that often found him sailing into the headlines. The third screen adaptation of Robert Penn Warren's influential novel, All the King's Men featured an impressive list of top-name Hollywood talent including Jude Law, Kate Winslet, Anthony Hopkins, Patricia Clarkson, James Gandolfini, and Mark Ruffalo. In 2008, Penn received the Academy Award for Best Actor for his performance in Milk, a biopic starring Penn in the role of politician and civil rights activist Harvey Milk. Shortly afterwards, Penn starred in Fair Game, an adaptation of author Valerie Plame's novel of the same name, and co-starred with Brad Pitt and Jessica Chastain in director Terrence Malick's critically acclaimed drama The Tree of Life in 2011. In 2013, he had a small role as gangster Mickey Cohen in Gangster Squad and a supporting role in The Secret Life of Walter Mitty.

Trivia: Known for his dark intensity and idiosyncratic performances, Benicio Del Toro became one of Hollywood's more unique actors. His looks suggesting a hidden background as Wednesday Addams' hunky older brother, he first became known to film audiences in 1995 with his breakthrough performance in The Usual Suspects. Born February 19, 1967 in Santurce, Puerto Rico, Del Toro was the son of lawyers. His mother died when he was nine, and, four years later, his father moved the family to Mercersberg, PA, where they lived on a farm. While attending the University of California at San Diego, where he was working toward a business degree, Del Toro took an acting class and was soon hooked. He appeared in a number of student productions, one of which led to a stint performing at a drama festival at New York's Lafayette Theatre. Del Toro decided to remain in New York to study acting at the Circle in the Square Acting School and won a scholarship to the Stella Adler Conservatory.A move to Los Angeles, where he studied at the Actors Circle Theatre, led to Del Toro's first television roles, which included a guest spot on Miami Vice and an appearance as a drug dealer on the miniseries Drug Wars: The Camarena Story (1990). The actor also began showing up in feature films, perhaps most notably as Duke the Dog-Faced Boy in Big Top Pee-wee (1988). Despite fairly steady work, Del Toro was still virtually unknown when he was cast as the eccentric criminal Fenster in Bryan Singer's The Usual Suspects. His slurred, otherworldly performance earned widespread praise, an Independent Spirit Award, and, coupled with the film's great success, Del Toro was soon thrust into the limelight that had hitherto eluded him. The actor followed up The Usual Suspects with a supporting role as the titular artist's best friend in Julian Schnabel's Basquiat (1996). Despite intriguing subject matter and a stellar cast, the film was something of a critical and commercial disappointment, although Del Toro's work did earn him a second Independent Spirit Award. Having thus put his trademark on offbeat character acting -- something that was also helped by his role as a gangster in Abel Ferrara's The Funeral (1996) -- Del Toro played a romantic lead opposite Alicia Silverstone in Excess Baggage (1997), a botched caper comedy that cast the actor as a bumbling car thief.Del Toro's next film, Terry Gilliam's much anticipated 1998 adaptation of Hunter S. Thompson's Fear and Loathing in Las Vegas, would receive an intensely mixed critical reception. A drug-addled, hallucinatory odyssey, it starred Del Toro as Dr. Gonzo, protagonist Raoul Duke's (Johnny Depp basically playing Thompson) partner in crime. Del Toro earned strong notices for his portrayal of the portly, freewheeling, Samoan lawyer (based on real-life Thompson cohort Oscar Acosta), and his performance was widely touted as one of the best aspects of the film. Del Torogained further notice when he won several awards -- including the Best Supporting Actor Golden Globe and Oscar -- for his role as a Mexican cop entangled in the international drug-trade war in Steven Soderbergh's Traffic (2000). The next year, Del Toro played a mentally disabled man wrongly accused of murder in director Sean Penn's sad tale of obsession, The Pledge, and earned his second Academy Award nomination for his performance in 21 Grams in 2003. Del Toro made his directorial debut in 2004, reuniting with Depp for an adaptation of another Hunter Thompson book, The Rum Diaries. He was also starred in Che (2008), Terrence Malick's biopic about Cuban revolutionary Che Guevara. This role led t many awards, including the Best Actor Award at the celebrated Cannes Film Festival. Later, in 2010, Del Toro starred in a remake of The Wolf Man, the classic creature feature from Lon Chaney, Jr.

Trivia: Staking claim on her fame with her role in the comedy-horror spoof Scary Movie, Regina Hall has frequented the big screen in roles that far from betrayed her age. Born in 1971 in Washington, D.C., Hall earned a degree in journalism from N.Y.U. before embarking on a film career. In 1997, she began appearing in commercials at age 26, and then made the giant leap into movies. Her recurring role in Scary Movie and the sequel Scary Movie 2 exhibited the 30-year-old's ability to maintain her youthful appearance, as she portrayed the high-school-aged Brenda Meeks. Hall's first film role had come in 1999 with a small role in Malcolm D. Lee's drama The Best Man. The following year, she made several film appearances, including her starring role in Scary Movie. In addition, she played small parts in two films directed by Gina Prince-Bythewood, the drama Love and Basketball, and the TV movie Disappearing Acts, featuring Sanaa Lathan and Wesley Snipes. In 2001, Hall's list of credits grew to include her first television role, as Corretta Lipp on the prime-time drama Ally McBeal, which was a recurring role for several episodes. Also that year, Scary Movie 2 was released, in addition to the Mandel Holland comedy The Other Brother, featuring Hall as Vicki. One year later, she starred in the action-drama Paid in Full, directed by Charles Stone III. She reprised her role as Brenda Meeks yet again for Scary Movie 3 (2003) and Scary Movie 4 (2006), and played a supporting role in the 2009 crime thriller Law Abiding Citizen. The following year she had some success for her supporting role in Neil LaBute's remake of Frank Oz's black comedy Death at a Funeral, in which she co-starred with Danny Glover, Peter Dinklage, and Martin Lawrence, among others. She co-starred with Kevin Hart and Michael Ealy in Think Like a Man (2012), which was adapted from Steve Harvey's non-fiction self-improvement book Act Like a Lady, Think Like a Man.