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(In parentheses is the number of dictionaries in which OneLook found the word.)

1. head (108)
2. header (57)
3. heading (49)
4. headache (47)
5. headway (36)
6. headland (35)
7. headed (34)
8. headline (34)
9. headroom (34)
10. headlight (33)
11. heady (33)
12. headband (32)
13. headless (32)
14. headdress (31)
15. headgear (31)
16. headquarters (31)
17. heads up (31)
18. headstone (31)
19. headstrong (31)
20. headlong (30)
21. headset (30)
22. headman (29)
23. headboard (28)
24. headship (28)
25. headstock (28)
26. head on (27)
27. headhunter (27)
28. headmaster (27)
29. headpiece (27)
30. headsman (27)
31. headwind (27)
32. headsail (26)
33. head-on (25)
34. headliner (25)
35. headlock (25)
36. headrest (25)
37. head off (24)
38. head over heels (24)
39. headcheese (24)
40. headlamp (24)
41. Heads (24)
42. headstand (24)
43. head start (23)
44. head to head (23)
45. headmistress (23)
46. heads-up (23)
47. headwaters (23)
48. headword (23)
49. head count (22)
50. head lice (22)
51. head of state (22)
52. head up (22)
53. headfirst (22)
54. headphones (22)
55. headspring (22)
56. headstall (22)
57. head cold (21)
58. head-to-head (20)
59. headnote (20)
60. headpin (20)
61. head of household (19)
62. head shop (19)
63. headphone (19)
64. headrace (19)
65. head sea (18)
66. headfish (18)
67. headscarf (18)
68. headshake (18)
69. head trip (17)
70. headhunt (17)
71. headspace (17)
72. head teacher (16)
73. headachy (16)
74. headmost (16)
75. headquarter (16)
76. headshot (16)
77. headstream (16)
78. headwaiter (16)
79. head honcho (15)
80. head injury (15)
81. head louse (15)
82. head voice (15)
83. headcount (15)
84. headhunting (15)
85. headiness (15)
86. headlines (15)
87. headmen (15)
88. headwork (15)
89. head cheese (14)
90. head covering (14)
91. head gate (14)
92. head hunter (14)
93. head nurse (14)
94. headbanger (14)
95. headful (14)
96. headily (14)
97. head crash (13)
98. head first (13)
99. head gasket (13)
100. head lettuce (13)

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