Abstract. We say that a digraph is essentially cyclic if its Laplacian spectrum is not completely real. The essential cyclicity implies the presence of directed cycles, but not vice versa. The problem of characterizing essential cyclicity in terms of graph topology is difficult and yet unsolved. Its solution is important for some applications of graph theory, including that in decentralized control. In the present paper, this problem is solved with respect to the class of digraphs with ring structure, which models some typical communication networks. It is shown that the digraphs in this class are essentially cyclic, except for certain specified digraphs. The main technical tool we employ is the Chebyshev polynomials of the second kind. A by-product of this study is a theorem on the zeros of polynomials that differ by one from the products of Chebyshev polynomials of the second kind. We also consider the problem of essential cyclicity for weighted digraphs and enumerate the spanning trees in some digraphs with ring structure.