Though he may have enjoyed cultivating his image as a boy from the wrong side of the tracks, British filmmaker Guy Ritchie was actually the son of successful advertising executive John Ritchie and, after his parents divorced, spent much of his youth at the 17th century home of his baronet stepfather, Sir Michael Leighton. His dyslexia made school a tough proposition, and he managed only a GCSE (General Certificate of Secondary Education) in film studies, knocking about as a laborer until finally setting his sights on a filmmaking career at age 25. Beginning as a film runner, he branched into directing music videos, doing "20 videos back to back, really crappy ones with sort of German rave bands" his first year. He may have abhorred the music, but he learned a lot about the camera and moved on to helm a couple commercials before directing a 20-minute short, "The Hard Case" (1995). When it aired on Channel 4, it caught the eye of Sting, whose wife Trudie Styler would serve as an executive producer of his 1998 feature directing debut, "Lock, Stock and Two Smoking Barrels". (Sting would make a cameo appearance.)
Possessing style to spare, Ritchie's glamorization of the tawdry world of East End crooks became one of that year's biggest home-grown successes in the United Kingdom, second only to "Sliding Doors", starring Gwyneth Paltrow. Though it didn't fare as well in the USA, it was not for lack of humor or plot twists that kept the clever caper movie from running out of steam in the final act. Ritchie scripted some wonderful characters with Damon Runyonesque names like Hatchet Harry (P.H. Moriarty), Barry the Baptist (Harry's "muscle" played by the late bare knuckles champion Lenny McLean) and Big Chris, a deadpan hitman essayed with panache by British soccer bad boy Vinnie Jones. He also wisely chose to play some of the most vicious acts of violence off camera, showing the ramifications while effectively distancing the viewer from the bloodshed. His accomplished first picture made him one of the hottest young directors around and earned Sony's backing for his second film, "Snatch" (2000), a return to the same colorful gangland milieu that featured Brad Pitt. Ritchie also co-scripted and produced that year's "Lock, Stock and Four Stolen Hooves", the pilot for the seven-part British TV series version of "Lock, Stock and Two Smoking Barrels" (for Channel 4).
Once Ritchie married and fathered a son with the decade-older multimedia megastar Madonna, an on-screen collaboration seemed inevitable. The couple started with baby steps, teaming for the stylish music video for her hit song "What It Feels Like for a Girl" and, later, the fast-paced and funny short film "Star," part of a five-episode series of car-oriented vignettes featured on the website for automaker BMW. The married duo finally hit the big screen together in 2002 when Ritchie directed his wife in the romantic comedy "Swept Away," a remake of Lina Wertmuller's 1974 Italian film of the same title, in which Madonna plays a spoiled rich woman marooned on a deserted island with a spirited sailor (Adriano Gainnini). Suffice to say, the film tanked; even landing on many a viewers' "worst movies of all time" lists. Cited as the film's biggest flaw - Madonna's acting ability, or lack thereof.