In December 1995, puzzlemaster Will Shortz challenged listeners of National Public Radio to write grammatical and understandable sentences that contained the same word four or more times in succession. The greatest number settled on the word will, which lends itself readily to such strings:

Will Will will Will his yacht? (Marianne Stambaugh)

So some got more ambitious:

Of his own free will, will Will will Will Jr. his dog? (Daniel Waldman)

Will, will Will will Will will to continue on? (Jennie Raymond)

The will Will will will Will will will Will to change his behavior. (Karan Talley)

Relatives wonder if the Will Will will will will Will Will Jr. any part of his father’s estate. (Alan Singer)

What will show how much affection Will had for Will? The will Will will will Will will: Will will will Will Will Shakespeare’s will! (Edgar Bley)

The purest entry came both from Jeff and Loni Doyle and from Bill Topazio — it concerns the bequest of G. Gordon Liddy’s 1980 autobiography:

Will Will will Will Will?

(A. Ross Eckler, “When There’s A Will …,” Word Ways 29:3 [August 1996], 151-155.)