All US bills carry the signatures of two officials, the Secretary of the Treasury and the United States Treasurer. Many different people have served in those positions so depending on when a bill was printed it will carry different signatures. If you look at the bills in your wallet you should find many examples of different signers.
It can be difficult to associate a bill's printing date with either the "series date" or signature combination shown on the front because the rules surrounding the selection of dates aren't hard and fast.
Up till 1974, a new series date was put on a bill only when there was a significant design change. Usually the first date in a series was "plain"; i.e. the series date appeared by itself. When a new Secretary of the Treasury or Treasurer took office, a small letter would be placed by the date, starting with "A", then "B", and so on. (That practice in itself confuses many people because it means "A" bills are the second set in a series, "B" bills are the third, and so on).
During the mid-20th century there was significant political inertia and outright resistance towards changing bills' designs. That resulted in absurdities such as $1 bills printed in the early 1960s carrying a 1935 date simply because the design was the same. Finally in 1974 the Treasury started modifying the practice so that a new series date would be used not only when a new design was adopted but also when a new Secretary of the Treasury took office. Letters would be added only when a new Treasurer was appointed. Series dates now change much more frequently and letters, which once ran as high as G or H, now usually end at A or B - if one is used at all.
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