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Pyrolysis oil has shown potential as an environmentally-friendly petroleum replacement for the production of fuel and chemicals. Also, the use of waste materials in the production of pyrolysis oil alleviates concerns associated with waste disposal. However, there are still challenges in application of pyrolysis oil as fuel and chemicals due to its convoluted composition and properties that make it incompatible with petroleum. Although analyses have been conducted to explore the composition of pyrolysis oils, complete and in-depth characterizations are required for efficient utilization. The work presented here utilizes chromatographic separations and multiple analysis methods to explore the complexity of pyrolysis oils and the differences between samples. The composition of pyrolysis oil is highly dependent on the material used for production. Plant and food materials (biomass) result in oils that are highly oxygenated causing high acidity and viscosity. Pyrolysis of plastic material results in an oil composed of paraffinic hydrocarbons with low oxygen content. When biomass and plastics are mixed in municipal waste, the pyrolysis oil shows a composition with characteristics of both starting components; lower aromaticity than biomass pyrolysis oils and higher oxygen content than plastic pyrolysis oils. Characterization of these different pyrolysis oils requires complementary, targeted analyses for complete coverage of all compositions in each unique sample. The high resolution and mass accuracy of Fourier transform ion cyclotron resonance mass spectrometry provides elemental formulas for the thousands of components within a pyrolysis oil. This method is particularly useful for the polar and high molecular weight species that are not compatible with gas chromatography. In contrast, gas chromatography is beneficial for the analysis of volatile components and provides structural information based on retention time. Infrared spectroscopy provides bulk functional information of an oil, and is especially helpful in identifying oxygen functionalities. To further explore the complexity of pyrolysis oils, solid phase extractions reduce complexity and allow for analysis of targeted chemistries without interference. Extractions also provide functional information based on the interaction of species within the sample with the stationary phase. Combination of methods in the analysis of both biomass- and municipal waste-derived pyrolysis oils provides a molecular level understanding of their compositions and properties, illuminating efficient applications for these oils.