Wilder himself was nominated for 21 Oscars®, winning six, three for screenplay (Double Indemnity, Sunset Boulevard, The Apartment), two for directing (Lost Weekend, The Apartment), one for producer of a best picture (The Apartment). Overall, Wilder won 48 awards out of 95 nominations.
- Sunset Boulevard (1950, bw) 9.2 No. 31 on IMDB 250 Three Oscars®, 16 awards overall
- Double Indemnity (1944, bw) 9.0 No. 53 on IMDB 250 7 Oscar® nominations, 0 wins
- Stalag 17 (1953, bw) 8.6 No. 209 on IMDB 250 1 Oscar®, actor for William Holden
- One, Two, Three (1961, bw) 8.8 (comedy) 1 Oscar® nomination, 5 others, 0 wins
- Some Like It Hot (1959, bw) 8.4 (comedy) No. 81 on IMDB 250 1 Oscar®, 11 awards overall
- The Apartment (1960, bw) 8.4 No. 91 on IMDB 250 Five Oscars®, 22 awards overall
- Witness For the Prosecution (1957, bw) 8.3 No. 129 on IMDB 250 Six Oscar® nominations, no wins, 6 awards overall
- The Seven Year Itch (1955) 8.2 (comedy) One award, Golden Globe for Tom Ewell, best actor
- Ace in the Hole (1951, bw) 8.1 Two awards Int'l Film award for Wilder at Venice
- The Fortune Cookie (1966, bw) 7.8 (comedy) Three awards, best supp. actor Oscar® for Walter Matthau
- The Major and the Minor (1942, bw) 7.6 (comedy)
The Lost Weekend should probably be on this list, but I find it so depressing that it's hard to recommend. But it did win the Oscar® for best picture, director (Wilder), and screenplay (Wilder and Charles Brackett), in 1946, for his first two academy awards.
Wilder's Oscar® nominations for picture (as producer): The Apartment [AA]
Wilder's Oscar® nominations for director: Double Indemnity, The Lost Weekend [AA], A Foreign Affair, Sunset Boulevard, Stalag 17, Sabrina, Witness For the Prosecution, Some Like It Hot, The Apartment [AA]
Wilder's Oscar® nominations for screenplay: Ninotchka, Ball of Fire, Hold Back the Dawn, Double Indemnity, The Lost Weekend [AA], A Foreign Affair, Sunset Boulevard [AA], Ace in the Hole, Sabrina, Some Like It Hot, The Apartment [AA]
Looking at that list of screeplays, he could have easily won 2-3 more Oscars - Ninotchka, Ball of Fire, Double Indemnity, Sunset Boulevard, Ace in the Hole, Some Like It Hot are all Oscar worthy to me.