| 100% | SISTER | 6 | Maggie Gyllenhaal, to Jake Gyllenhaal |
| 100% | SIS | 3 | Maggie Gyllenhaal, to Jake Gyllenhaal |
| 89% | SISTER | 6 | Relation of Maggie to Jake Gyllenhaal |
| 62% | EXES | 4 | Joe Jonas and Jake Gyllenhaal, to Taylor Swift |
| 57% | JAMIELEECURTIS | 14 | "Halloween" actress who is godmother to "Jarhead" actor Jake Gyllenhaal: 3 wds. |
| 53% | ALL | 3 | "___ Too Well," 2012 song by Taylor Swift rumored to be about her romance with Jake Gyllenhaal |
| 50% | DARKO | 5 | Donnie played by Jake Gyllenhaal |
| 50% | JARHEAD | 7 | Jake Gyllenhaal film |
| 49% | JAKE | 4 | Maggie Gyllenhaal's brother |
| 48% | LOVE | 4 | Jake Gyllenhaal film "___ & Other Drugs" |
| 48% | JAKE | 4 | Maggie Gyllenhaal's actor brother |
| 47% | SIS | 3 | Maggie, to Bart |
| 47% | SIS | 3 | Maggie, to Lisa |
| 46% | STEPHEN | 7 | Jake Gyllenhaal's film director father |
| 45% | DARKO | 5 | Jake Gyllenhaal starrer science fiction film "Donnie ___" |
| 45% | MAGGIE | 6 | __ and Jake Gyllenhaal, acting siblings |
| 45% | DARKO | 5 | "Donnie ___" (2001 Jake Gyllenhaal film) |
| 44% | JARHEAD | 7 | Jake Gyllenhaal movie about a U.S. Marine |
| 44% | SOURCECODE | 10 | 2011 Jake Gyllenhaal sci-fi mystery |
| 44% | OTHER | 5 | "Love & ___ Drugs" (2010 Jake Gyllenhaal romcom) |
| 44% | DARKO | 5 | Donnie ___, title role for Jake Gyllenhaal |
| 44% | DARKO | 5 | “Donnie ___” (early film for Jake Gyllenhaal) |
| 42% | BRO | 3 | Bart, to Maggie |
| 42% | MOM | 3 | Marge, to Maggie |
| 42% | OCTOBERSKY | 10 | 1999 biopic starring Jake Gyllenhaal as Homer Hickam |
| 42% | BROTHERS | 8 | 2009 drama starring Jake Gyllenhaal and Natalie Portman |
| 42% | ZODIAC | 6 | 2007 Jake Gyllenhaal film about a serial killer |
| 42% | DARKO | 5 | "Donnie ___," 2001 sci-fi film starring Jake Gyllenhaal |
| 42% | DARKO | 5 | Title character of a Jake Gyllenhaal cult classic |
| 41% | HALFSISTER | 10 | Maggie or Lexie, to Meredith Grey |