Beethoven's rich compositional language evokes unique problems that have fueled scholarly dialogue for many years. My analyses focus on two types of paradoxes as central compositional problems in some of Beethoven's symphonic pieces and piano sonatas. My readings of Beethoven's Piano Sonata No. 27 (Op. 90), Symphony No. 4 (Op. 60), and Symphony No. 8 (Op. 93) explore the nature and significance of paradoxical unresolved six-four chords and their impact on tonal structure. I consider formal-tonal paradoxes in Beethoven's Tempest Sonata (Op. 31, No. 2), Ninth Symphony (Op. 125), and Overture die Weihe des Hauses (Op. 124). Movements that evoke formal-tonal paradoxes retain the structural framework of a paradigmatic interrupted structure, but contain unique voice-leading features that superimpose an undivided structure on top of the "residual" interrupted structure. Carl Schachter's observations about "genuine double meaning" and his arguments about the interplay between design and tonal structure in "Either/Or" establish the foundation for my analytical approach to paradox. Timothy Jackson's reading of Brahms' "Immer leiser word meine Schlummer" (Op. 105, No. 2) and Stephen Slottow's "Von einem Kunstler: Shapes in the Clouds" both clarify the methodology employed here. My interpretation of paradox involves more than just a slight contradiction between two Schenkerian readings; it involves fundamentally opposed readings, that both result from valid, logical lines of analytical reasoning. In my view, paradoxes could be considered a central part of Beethoven's persona and philosophy. Beethoven's romantic endeavors and his relationships with mentors suggest that paradoxes might have been central to his bravura. Furthermore, Beethoven's familiarity with the politics of the French Revolution and Shakespearean literature suggest that paradoxes in some pieces (including the Ninth Symphony) could be metaphorical representations of his ideology. However, I do not attempt to explicitly link specific style features to extra-musical ideas. Modern Schenkerian scholars continue to expand and refine Schenker's formal-tonal models as well as his concept of interruption. In my view, by considering paradox as a focal compositional problem, we can better understand some of the formal-tonal issues and shifting allegiances in Beethoven's music and take another step beyond the rigidity of some paradigmatic formal-tonal prototypes.