I have not seen any of the other four Oscar nominees, which were Elizabeth, Life Is Beautiful, Saving Private Ryan and The Thin Red Line. That was the year I lived in Bosnia and then Croatia, so I have seen very few films from 1998; apart from the Oscar and Hugo winners, I have watched There's Something About Mary, Sliding Doors, Primary Colors, Bulworth, Playing by Heart and that's it. I like all of these, Bulworth least and, I'll be honest, Shakespeare in Love most.
IMDB users, as so often, take a different view, ranking it only 15th on one ranking and an incredibly low 44th on the other, which is a worse aggregate ranking than any Oscar winner since Cavalcade (slightly worse than Tom Jones). The Big Lebowski and Saving Private Ryan top the two counts. Among the allegations about Harvey Weinstein is the story that he lobbied mercilessly to get Shakespeare in Love its nomination and win ahead of Saving Private Ryan, but to be honest it's entirely in character for Oscar voters to go for the big warm-hearted romantic tale ahead of a gritty reality-based war film. (I admit that they have sometimes made the other choice.)
Here's a trailer.
Because this is a film made with mainly British actors in 1999, loads and loads of the cast have also been in Doctor Who, one of whom was also in an Oscar-winning film. That one is Simon Callow, here the randy Master of the Revels, previously impresario Emanuel Schikaneder in Amadeus, and also of course Charles Dickens in The Unquiet Dead, the third episode of New Who.
The only representative of Old Who is Martin Clunes, here Richard Burbage, previously the spoiled aristocratic Lon in an early appearance in the Fifth Doctor story Snakedance.
Mark Williams, the stuttering tailor Wabash here, went on to be Rory Williams' father in several Eleventh Doctor stories.
Barnaby Kay is Nol here and went on to be the Viking Heidi in The Girl Who Died:
And Nicholas Boulton is the actor Condell here and the Businessman in the Tenth Doctor story Gridlock.
I love Imelda Staunton, the nurse here and the invisible voice of the computer in The Girl Who Waited.
As noted above, this film is far from most people's top ten films of 1999, and you may not have seen it. It's a romantic comedy - the first comedy to win Best Picture since Annie Hall, more than twenty years before - set in Merrie England, which was the setting of a spate of Oscar-winners in the 1960s but has since been visited only for parts of Chariots of Fire (which is perhaps too late to be Merrie). The plot is that beautiful (and completely fictional) Viola de Lesseps is in love with young playwright William Shakespeare, disguises herself as a man in order to join his theatre company, and the two of them end up playing the lead roles in the first ever performance of Romeo and Juliet. This is surely the first Oscar-winning film about the writer of a previous Oscar-winning film. The two leads, played by Gwyneth Paltrow and Joseph Fiennes, are tremendously watchable, and I think there's more sex in this film than in all the previous 70 Oscar-winning films combined.
(I'm going to pause to recommend the Arkangel audio of Romeo and Juliet. Romeo is Joseph Fiennes (who plays Shakespeare himself in Shakespeare in Love) and Juliet is Maria Miles (Elfine in Cold Comfort Farm). But both are somewhat overshadowed by three excellent supporting performances: Clive Swift (who has been in Doctor Who three times over the years) doubling up as both Friar Laurence and the Chorus; Elizabeth Spriggs (who was, among other things, one of the cannibalistic old ladies in Paradise Towers) as Juliet's Nurse, and best of all, Mercutio is played, in his native Scottish accent, by David Tennant. You can get it here.)
I guess I should try and do my usual thing of going from the bits I didn't like to the bits I did, but really, there's very little to dislike here. Historical purists will complain that it's hugely inaccurate in terms of what people wore, said and did in England in the 1590s, and I would add (as I must) that there actually were non-white people in London then and had been for centuries. Fine. It's entertainment, not education. It's very funny and the music is great.
As mentioned, Judi Dench is only in it for 8 minutes, but my god does she dominate those 8 minutes.
I think one has to admit that Paltrow and Dench somewhat overshadow Fiennes and the other male actors, good as they are. Again, fine. Too many romances portray the woman as lacking agency; Viola here challenges convention and while she is not ultimately completely successful, the point has been made.
I'm surprised by how far up my ranking I'm putting this - just outside the top ten, below Rain Man but above Terms of Endearment.
Next up is American Beauty, which I actually saw in the cinema when it came out.
1920s: Wings (1927-28) | The Broadway Melody (1928-29)
1930s: All Quiet on the Western Front (1929-30) | Cimarron (1930-31) | Grand Hotel (1931-32) | Cavalcade (1932-33) | It Happened One Night (1934) | Mutiny on the Bounty (1935, and books) | The Great Ziegfeld (1936) | The Life of Emile Zola (1937) | You Can't Take It with You (1938) | Gone with the Wind (1939, and book)
1940s: Rebecca (1940) | How Green Was My Valley (1941) | Mrs. Miniver (1942) | Casablanca (1943) | Going My Way (1944) | The Lost Weekend (1945) | The Best Years of Our Lives (1946) | Gentleman's Agreement (1947) | Hamlet (1948) | All the King's Men (1949)
1950s: All About Eve (1950) | An American in Paris (1951) | The Greatest Show on Earth (1952) | From Here to Eternity (1953) | On The Waterfront (1954, and book) | Marty (1955) | Around the World in Eighty Days (1956) | The Bridge on the River Kwai (1957) | Gigi (1958) | Ben-Hur (1959)
1960s: The Apartment (1960) | West Side Story (1961) | Lawrence of Arabia (1962) | Tom Jones (1963) | My Fair Lady (1964) | The Sound of Music (1965) | A Man for All Seasons (1966) | In the Heat of the Night (1967) | Oliver! (1968) | Midnight Cowboy (1969)
1970s: Patton (1970) | The French Connection (1971) | The Godfather (1972) | The Sting (1973) | The Godfather, Part II (1974) | One Flew Over the Cuckoo's Nest (1975) | Rocky (1976) | Annie Hall (1977) | The Deer Hunter (1978) | Kramer vs. Kramer (1979)
1980s: Ordinary People (1980) | Chariots of Fire (1981) | Gandhi (1982) | Terms of Endearment (1983) | Amadeus (1984) | Out of Africa (1985) | Platoon (1986) | The Last Emperor (1987) | Rain Man (1988) | Driving Miss Daisy (1989)
1990s: Dances With Wolves (1990) | The Silence of the Lambs (1991) | Unforgiven (1992) | Schindler's List (1993) | Forrest Gump (1994) | Braveheart (1995) | The English Patient (1996) | Titanic (1997) | Shakespeare in Love (1998) | American Beauty (1999)
21st century: Gladiator (2000) | A Beautiful Mind (2001) | Chicago (2002)